| Date | Time | Type | Home School | Away School | Site |
| TUE 8/19 | 3:00 PM | League | Bunnell | Joel Barlow | Bunnell HS - Blackhawk Country Club (Old OCC) |
| TUE 8/19 | 3:00 PM | League | Newtown | Immaculate | Rock Ridge Country Club - Rock Ridge Country Club |
| TUE 8/19 | 3:00 PM | Non-League | Stratford | St. Joseph | Mill River Country Club - Mill River Country Club |
| TUE 8/19 | 3:15 PM | League | Wilton | Norwalk | Rolling Hills Country Club - Rolling Hills Country Club |
| TUE 8/19 | 3:15 PM | Non-League | Weston | Bethel | Weston High School - Aspetuck Country Club |
| WED 8/20 | 11:00 AM | Non-League | Pomperaug | New Milford | Pomperaug High School - Highfield Country Club |
| WED 8/20 | 2:00 PM | League | Notre Dame Prep | Joel Barlow | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| WED 8/20 | 3:00 PM | League | Westhill | Ridgefield | EG Brennan Golf Course - E Gaynor Brennan Golf Course |
| WED 8/20 | 3:00 PM | League | Brien McMahon | Wilton | Oak Hills Golf Course - Oak Hills Golf Course |
| WED 8/20 | 3:00 PM | Non-League | Bethel | Masuk | Bethel High School - Connecticut Country Club |
| WED 8/20 | 3:00 PM | Non-League | Bunnell | Stratford | Bunnell HS - Blackhawk Country Club (Old OCC) |
| WED 8/20 | 3:15 PM | League | Staples | Danbury | Longshore Golf Course - Longshore Golf Course |
| WED 8/20 | 3:30 PM | League | Fairfield Prep | Wethersfield | CC of Fairfield - CC of Fairfield |
| THU 8/21 | 2:15 PM | League | Danbury | Wilton | Richter Park Golf Course - Richter Park Golf Course |
| THU 8/21 | 2:51 PM | League | Fairfield Ludlowe | Norwalk | Smith Richardson Golf Course - Smith Richardson Golf Course |
| THU 8/21 | 3:00 PM | League | Notre Dame Prep | Bunnell | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| THU 8/21 | 3:00 PM | League | Newington | New Britain | Indian Hill Country Club - Indian Hill Country Club |
| THU 8/21 | 3:00 PM | League | Lakeview | Housatonic Regional | Lakeview Regional High School - Litchfield Country Club (LCC) |
| THU 8/21 | 3:00 PM | League | Joel Barlow | Stratford | Redding Country Club - Redding Country Club |
| THU 8/21 | 3:00 PM | League | Hall | Avon | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 8/21 | 3:00 PM | League | Simsbury | Conard | Simsbury High School - Simsbury Farms CC |
| THU 8/21 | 3:00 PM | League | Berlin | Wethersfield | Timberlin Golf Course - Timberlin Golf Course |
| THU 8/21 | 3:00 PM | League | Northwest Catholic | Lewis Mills | Wampanoag Country Club - Wampanoag Country Club |
| THU 8/21 | 3:00 PM | Non-League | New Fairfield | Newtown | Club River Oaks - Club River Oaks |
| THU 8/21 | 3:00 PM | Non-League | Masuk | Weston | Whitney Farms Golf Course - Whitney Farms Golf Course |
| THU 8/21 | 3:15 PM | League | Trumbull | Stamford | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| THU 8/21 | 3:30 PM | League | Ridgefield | Greenwich | Ridgefield Golf Course - Ridgefield Golf Course |
| FRI 8/22 | 10:30 AM | Non-League | New Milford | Brookfield | Candlewood Valley Country Club - Candlewood Valley Country Club |
| MON 8/25 | 3:00 PM | League | Notre Dame Prep | Stratford | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| MON 8/25 | 3:00 PM | League | Newington | Rocky Hill | Indian Hill Country Club - Indian Hill Country Club |
| MON 8/25 | 3:00 PM | League | Joel Barlow | Brookfield | Redding Country Club - Redding Country Club |
| MON 8/25 | 3:00 PM | League | Stamford | Danbury | Stamford High - Sterling Farms Golf Course |
| MON 8/25 | 3:00 PM | League | Masuk | Bunnell | Whitney Farms Golf Course - Whitney Farms Golf Course |
| MON 8/25 | 3:15 PM | League | Weston | Newtown | Weston High School - Aspetuck Country Club |
| TUE 8/26 | 2:20 PM | League | Stamford | Ridgefield | Stamford High - Sterling Farms Golf Course |
| TUE 8/26 | 3:00 PM | League | New Fairfield | Pomperaug | Club River Oaks - Club River Oaks |
| TUE 8/26 | 3:00 PM | League | Westhill | New Canaan | EG Brennan Golf Course - E Gaynor Brennan Golf Course |
| TUE 8/26 | 3:00 PM | League | Windsor | New Britain | Goodwin Park Golf Course - Goodwin Park Golf Course |
| TUE 8/26 | 3:00 PM | League | Lewis Mills | Farmington | Lewis Mills High School - Fairview Farm Golf Course |
| TUE 8/26 | 3:00 PM | League | Stratford | Bethel | Mill River Country Club - Mill River Country Club |
| TUE 8/26 | 3:00 PM | League | Norwalk | Staples | Oak Hills Golf Course - Oak Hills Golf Course |
| TUE 8/26 | 3:00 PM | League | Joel Barlow | Weston | Redding Country Club - Redding Country Club |
| TUE 8/26 | 3:00 PM | League | Immaculate | New Milford | Richter Park Golf Course - Richter Park Golf Course |
| TUE 8/26 | 3:00 PM | League | Conard | Southington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 8/26 | 3:00 PM | League | Simsbury | Avon | Simsbury High School - Simsbury Farms CC |
| TUE 8/26 | 3:00 PM | League | Fairfield Ludlowe | Brien McMahon | Smith Richardson Golf Course - Smith Richardson Golf Course |
| TUE 8/26 | 3:00 PM | League | Northwest Catholic | Hall | Wampanoag Country Club - Wampanoag Country Club |
| TUE 8/26 | 3:00 PM | League | Wethersfield | Glastonbury | Wethersfield Country Club - Wethersfield Country Club |
| TUE 8/26 | 3:15 PM | League | Trumbull | St. Joseph | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 8/27 | 3:00 PM | League | Bunnell | New Fairfield | Bunnell HS - Blackhawk Country Club (Old OCC) |
| WED 8/27 | 3:00 PM | League | New Milford | Weston | Candlewood Valley Country Club - Candlewood Valley Country Club |
| WED 8/27 | 3:00 PM | League | Westhill | Fairfield Ludlowe | EG Brennan Golf Course - E Gaynor Brennan Golf Course |
| WED 8/27 | 3:00 PM | League | Glastonbury | New Britain, Windsor | Minnechaug Golf Course - Minnechaug Golf Course |
| WED 8/27 | 3:00 PM | League | Brien McMahon | Greenwich | Oak Hills Golf Course - Oak Hills Golf Course |
| WED 8/27 | 3:00 PM | League | Norwalk | Greenwich | Oak Hills Golf Course - Oak Hills Golf Course |
| WED 8/27 | 3:00 PM | League | Darien | Fairfield Warde | Wee Burn CC - Wee Burn CC |
| WED 8/27 | 3:00 PM | Non-League | St. Joseph | Masuk | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 8/27 | 3:30 PM | League | New Canaan | Wilton | New Canaan HS - CCNC |
| THU 8/28 | 3:00 PM | League | Notre Dame Prep | Masuk | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| THU 8/28 | 3:00 PM | League | Lakeview | Northwestern | Lakeview Regional High School - Litchfield Country Club (LCC) |
| THU 8/28 | 3:00 PM | League | Lewis Mills | Simsbury | Lewis Mills High School - Fairview Farm Golf Course |
| THU 8/28 | 3:00 PM | League | New Canaan | Darien | New Canaan HS - CCNC |
| THU 8/28 | 3:00 PM | League | Immaculate | Pomperaug | Richter Park Golf Course - Richter Park Golf Course |
| THU 8/28 | 3:00 PM | League | Ridgefield | Norwalk | Ridgefield Golf Course - Ridgefield Golf Course |
| THU 8/28 | 3:00 PM | League | Hall | Southington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 8/28 | 3:00 PM | League | Fairfield Warde | St. Joseph | Smith Richardson Golf Course - Smith Richardson Golf Course |
| THU 8/28 | 3:00 PM | League | New Britain | Wethersfield | Stanley Golf Course - Stanley Golf Course |
| THU 8/28 | 3:00 PM | League | Avon | Newington, Farmington | The Golf Club of Avon - The Golf Club of Avon |
| THU 8/28 | 3:00 PM | League | Northwest Catholic | Conard | Wampanoag Country Club - Wampanoag Country Club |
| THU 8/28 | 3:15 PM | League | Greenwich | Danbury | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| THU 8/28 | 3:15 PM | League | Trumbull | Fairfield Ludlowe | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| TUE 9/2 | 2:20 PM | League | Immaculate | Newtown | Richter Park Golf Course - Richter Park Golf Course |
| TUE 9/2 | 2:20 PM | League | Stamford | Fairfield Ludlowe | Stamford High - Sterling Farms Golf Course |
| TUE 9/2 | 2:30 PM | League | Danbury | Ridgefield | Richter Park Golf Course - Richter Park Golf Course |
| TUE 9/2 | 3:00 PM | League | Bethel | Notre Dame Prep | Bethel High School - Connecticut Country Club |
| TUE 9/2 | 3:00 PM | League | Bunnell | New Milford | Bunnell HS - Blackhawk Country Club (Old OCC) |
| TUE 9/2 | 3:00 PM | League | Nonnewaug | Shepaug Valley | Crestbrook Park - Crestbrook Park Golf |
| TUE 9/2 | 3:00 PM | League | Gilbert | Thomaston | Green woods Country Club - Green woods Country Club |
| TUE 9/2 | 3:00 PM | League | Newington | Fairfield Prep | Indian Hill Country Club - Indian Hill Country Club |
| TUE 9/2 | 3:00 PM | League | Lakeview | Housatonic Regional | Lakeview Regional High School - Litchfield Country Club (LCC) |
| TUE 9/2 | 3:00 PM | League | Norwalk | Westhill | Oak Hills Golf Course - Oak Hills Golf Course |
| TUE 9/2 | 3:00 PM | League | Conard | Farmington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 9/2 | 3:00 PM | League | Simsbury | Hall | Simsbury High School - Simsbury Farms CC |
| TUE 9/2 | 3:00 PM | League | Southington | Lewis Mills | Southington High School - Southington Country Club |
| TUE 9/2 | 3:00 PM | League | Avon | Northwest Catholic | The Golf Club of Avon - The Golf Club of Avon |
| TUE 9/2 | 3:00 PM | League | Darien | Wilton | Woodway Country Club - Woodway Country Club |
| TUE 9/2 | 3:15 PM | League | Staples | Brien McMahon | Longshore Golf Course - Longshore Golf Course |
| TUE 9/2 | 3:15 PM | League | Weston | Masuk | Weston High School - Aspetuck Country Club |
| TUE 9/2 | 3:30 PM | League | New Canaan | Greenwich | New Canaan HS - CCNC |
| WED 9/3 | 3:00 PM | League | Housatonic Regional | Northwestern | Canaan Country Club - Canaan Country Club |
| WED 9/3 | 3:00 PM | League | Westhill | Danbury | EG Brennan Golf Course - E Gaynor Brennan Golf Course |
| WED 9/3 | 3:00 PM | League | Brien McMahon | Fairfield Warde | Oak Hills Golf Course - Oak Hills Golf Course |
| WED 9/3 | 3:00 PM | League | Pomperaug | Bethel | Pomperaug High School - Highfield Country Club |
| WED 9/3 | 3:00 PM | League | Joel Barlow | Notre Dame Prep | Redding Country Club - Redding Country Club |
| WED 9/3 | 3:00 PM | League | Fairfield Ludlowe | Darien | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 9/3 | 3:00 PM | League | Brookfield | Immaculate | Sunset Hill Golf Course - Sunset Hill Golf Course |
| WED 9/3 | 3:00 PM | Non-League | New Milford | Shepaug Valley | Candlewood Valley Country Club - Candlewood Valley Country Club |
| WED 9/3 | 3:00 PM | Non-League | Simsbury | Rocky Hill | Simsbury High School - Simsbury Farms CC |
| WED 9/3 | 3:10 PM | League | Greenwich | Trumbull | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| WED 9/3 | 3:10 PM | League | St. Joseph | Wilton | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 9/3 | 3:15 PM | League | Weston | Stratford | Weston High School - Aspetuck Country Club |
| WED 9/3 | 3:30 PM | League | New Canaan | Norwalk | New Canaan HS - CCNC |
| WED 9/3 | 3:30 PM | League | Newtown | New Fairfield | Rock Ridge Country Club - Rock Ridge Country Club |
| THU 9/4 | 2:51 PM | League | Fairfield Warde | Danbury | Smith Richardson Golf Course - Smith Richardson Golf Course |
| THU 9/4 | 3:00 PM | League | Bunnell | Pomperaug | Bunnell HS - Blackhawk Country Club (Old OCC) |
| THU 9/4 | 3:00 PM | League | Housatonic Regional | Gilbert | Canaan Country Club - Canaan Country Club |
| THU 9/4 | 3:00 PM | League | Glastonbury | Newington | Glastonbury Hills Country Club - Glastonbury Hills Country Club |
| THU 9/4 | 3:00 PM | League | Lewis Mills | Avon | Lewis Mills High School - Fairview Farm Golf Course |
| THU 9/4 | 3:00 PM | League | Northwestern | Nonnewaug | Northwestern Regional H.S. - Norfolk CC |
| THU 9/4 | 3:00 PM | League | Joel Barlow | Bethel | Redding Country Club - Redding Country Club |
| THU 9/4 | 3:00 PM | League | Conard | Hall | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 9/4 | 3:00 PM | League | Rocky Hill | Wethersfield | Rocky Hill High School - Stanley Golf Course |
| THU 9/4 | 3:00 PM | League | Brookfield | Stratford | Sunset Hill Golf Course - Sunset Hill Golf Course |
| THU 9/4 | 3:00 PM | League | Farmington | Simsbury | Tunxis Country Club - Tunxis Country Club |
| THU 9/4 | 3:00 PM | League | Northwest Catholic | Southington | Wampanoag Country Club - Wampanoag Country Club |
| THU 9/4 | 3:00 PM | League | Shepaug Valley | Lakeview | Washington Club Golf Course - Washington Club Golf Course |
| THU 9/4 | 3:00 PM | League | Masuk | New Fairfield | Whitney Farms Golf Course - Whitney Farms Golf Course |
| THU 9/4 | 3:10 PM | League | Greenwich | Fairfield Ludlowe | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| THU 9/4 | 3:10 PM | League | St. Joseph | Ridgefield | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| THU 9/4 | 3:15 PM | League | Staples | Westhill | Longshore Golf Course - Longshore Golf Course |
| THU 9/4 | 3:30 PM | League | New Canaan | Stamford | New Canaan HS - CCNC |
| MON 9/8 | 3:00 PM | League | Thomaston | Housatonic Regional | Crestbrook Park - Crestbrook Park Golf |
| MON 9/8 | 3:00 PM | League | Gilbert | Shepaug Valley | Green woods Country Club - Green woods Country Club |
| MON 9/8 | 3:00 PM | League | Lakeview | Northwestern | Lakeview Regional High School - Litchfield Country Club (LCC) |
| MON 9/8 | 3:00 PM | League | Joel Barlow | Pomperaug | Redding Country Club - Redding Country Club |
| MON 9/8 | 3:00 PM | League | Wethersfield | Windsor, Newington | Wethersfield Country Club - Wethersfield Country Club |
| MON 9/8 | 3:15 PM | League | Wilton | Greenwich | Rolling Hills Country Club - Rolling Hills Country Club |
| MON 9/8 | 3:20 PM | League | Immaculate | Weston | Richter Park Golf Course - Richter Park Golf Course |
| MON 9/8 | 3:30 PM | League | Newtown | Stratford | Rock Ridge Country Club - Rock Ridge Country Club |
| TUE 9/9 | 2:20 PM | League | Stamford | St. Joseph | Stamford High - Sterling Farms Golf Course |
| TUE 9/9 | 2:30 PM | League | Danbury | Darien | Richter Park Golf Course - Richter Park Golf Course |
| TUE 9/9 | 3:00 PM | League | Bunnell | Newtown | Bunnell HS - Blackhawk Country Club (Old OCC) |
| TUE 9/9 | 3:00 PM | League | New Fairfield | Notre Dame Prep | Club River Oaks - Club River Oaks |
| TUE 9/9 | 3:00 PM | League | Nonnewaug | Lakeview | Crestbrook Park - Crestbrook Park Golf |
| TUE 9/9 | 3:00 PM | League | Glastonbury | Rocky Hill | Glastonbury Hills Country Club - Glastonbury Hills Country Club |
| TUE 9/9 | 3:00 PM | League | Stratford | Immaculate | Mill River Country Club - Mill River Country Club |
| TUE 9/9 | 3:00 PM | League | Northwestern | Gilbert | Northwestern Regional H.S. - Norfolk CC |
| TUE 9/9 | 3:00 PM | League | Norwalk | Fairfield Warde | Oak Hills Golf Course - Oak Hills Golf Course |
| TUE 9/9 | 3:00 PM | League | Ridgefield | New Canaan | Ridgefield Golf Course - Ridgefield Golf Course |
| TUE 9/9 | 3:00 PM | League | Conard | Lewis Mills | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 9/9 | 3:00 PM | League | Simsbury | Northwest Catholic | Simsbury High School - Simsbury Farms CC |
| TUE 9/9 | 3:00 PM | League | New Britain | Berlin | Stanley Golf Course - Stanley Golf Course |
| TUE 9/9 | 3:00 PM | League | Farmington | Hall | Tunxis Country Club - Tunxis Country Club |
| TUE 9/9 | 3:00 PM | League | Shepaug Valley | Thomaston | Washington Club Golf Course - Washington Club Golf Course |
| TUE 9/9 | 3:00 PM | League | Masuk | Brookfield | Whitney Farms Golf Course - Whitney Farms Golf Course |
| TUE 9/9 | 3:15 PM | League | Trumbull | Brien McMahon | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 9/10 | 2:30 PM | League | Avon | Southington | The Golf Club of Avon - The Golf Club of Avon |
| WED 9/10 | 2:51 PM | League | Fairfield Warde | Westhill | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 9/10 | 3:00 PM | League | Housatonic Regional | Shepaug Valley | Canaan Country Club - Canaan Country Club |
| WED 9/10 | 3:00 PM | League | New Milford | Pomperaug | Candlewood Valley Country Club - Candlewood Valley Country Club |
| WED 9/10 | 3:00 PM | League | Brien McMahon | Darien | Oak Hills Golf Course - Oak Hills Golf Course |
| WED 9/10 | 3:00 PM | League | Stamford | Staples | Stamford High - Sterling Farms Golf Course |
| WED 9/10 | 3:00 PM | League | New Britain | Glastonbury | Stanley Golf Course - Stanley Golf Course |
| WED 9/10 | 3:00 PM | League | Berlin | Rocky Hill | Timberlin Golf Course - Timberlin Golf Course |
| WED 9/10 | 3:10 PM | League | Greenwich | St. Joseph | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| WED 9/10 | 3:30 PM | League | New Canaan | Fairfield Prep | New Canaan HS - CCNC |
| WED 9/10 | 3:30 PM | League | Newtown | Joel Barlow | Rock Ridge Country Club - Rock Ridge Country Club |
| THU 9/11 | 2:30 PM | League | Danbury | Norwalk | Richter Park Golf Course - Richter Park Golf Course |
| THU 9/11 | 3:00 PM | League | Brookfield | New Fairfield | Candlewood Valley Country Club - Candlewood Valley Country Club |
| THU 9/11 | 3:00 PM | League | Thomaston | Northwestern | Crestbrook Park - Crestbrook Park Golf |
| THU 9/11 | 3:00 PM | League | Gilbert | Nonnewaug | Green woods Country Club - Green woods Country Club |
| THU 9/11 | 3:00 PM | League | Ridgefield | Darien | Ridgefield Golf Course - Ridgefield Golf Course |
| THU 9/11 | 3:00 PM | League | Hall | Lewis Mills | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 9/11 | 3:00 PM | League | Simsbury | Southington | Simsbury High School - Simsbury Farms CC |
| THU 9/11 | 3:00 PM | League | Fairfield Warde | Staples | Smith Richardson Golf Course - Smith Richardson Golf Course |
| THU 9/11 | 3:00 PM | League | Rocky Hill | New Britain | Stanley Golf Course - Stanley Golf Course |
| THU 9/11 | 3:00 PM | League | Avon | Conard, Wethersfield | The Golf Club of Avon - The Golf Club of Avon |
| THU 9/11 | 3:00 PM | League | Berlin | Glastonbury | Timberlin Golf Course - Timberlin Golf Course |
| THU 9/11 | 3:00 PM | League | Farmington | Northwest Catholic | Tunxis Country Club - Tunxis Country Club |
| THU 9/11 | 3:00 PM | League | Masuk | New Milford | Whitney Farms Golf Course - Whitney Farms Golf Course |
| THU 9/11 | 3:10 PM | League | Greenwich | Stamford | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| THU 9/11 | 3:10 PM | League | St. Joseph | Fairfield Ludlowe | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| THU 9/11 | 3:15 PM | League | Fairfield Prep | Newtown | CC of Fairfield - CC of Fairfield |
| THU 9/11 | 3:30 PM | League | New Canaan | Trumbull | New Canaan HS - CCNC |
| FRI 9/12 | 3:00 PM | Non-League | Notre Dame Prep | Brookfield | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| MON 9/15 | 11:00 AM | Tournament | Berlin | Pomperaug, Wethersfield, Glastonbury, Newington, Farmington, Fairfield Prep, Avon, Conard | Timberlin Golf Course - Timberlin Golf Course |
| MON 9/15 | 2:30 PM | League | Windsor | Rocky Hill | Keney Park Golf Course - Keney Park Golf Course |
| MON 9/15 | 3:00 PM | League | Housatonic Regional | Northwestern | Canaan Country Club - Canaan Country Club |
| MON 9/15 | 3:00 PM | League | Nonnewaug | Thomaston | Crestbrook Park - Crestbrook Park Golf |
| MON 9/15 | 3:00 PM | League | Notre Dame Prep | Brookfield | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| MON 9/15 | 3:00 PM | League | Shepaug Valley | New Milford | Lake Waramaug Country Club - Lake Waramaug Country Club |
| MON 9/15 | 3:00 PM | League | Lakeview | Gilbert | Lakeview Regional High School - Litchfield Country Club (LCC) |
| MON 9/15 | 3:00 PM | League | Stratford | Joel Barlow | Mill River Country Club - Mill River Country Club |
| MON 9/15 | 3:00 PM | League | Darien | Greenwich | Wee Burn CC - Wee Burn CC |
| MON 9/15 | 3:15 PM | League | Staples | Ridgefield | Longshore Golf Course - Longshore Golf Course |
| MON 9/15 | 3:15 PM | League | Weston | Bunnell | Weston High School - Aspetuck Country Club |
| TUE 9/16 | 2:20 PM | League | Stamford | Brien McMahon | Stamford High - Sterling Farms Golf Course |
| TUE 9/16 | 2:30 PM | League | Danbury | New Canaan | Richter Park Golf Course - Richter Park Golf Course |
| TUE 9/16 | 3:00 PM | League | Bethel | New Milford | Bethel High School - Connecticut Country Club |
| TUE 9/16 | 3:00 PM | League | Housatonic Regional | Nonnewaug | Canaan Country Club - Canaan Country Club |
| TUE 9/16 | 3:00 PM | League | New Fairfield | Weston | Club River Oaks - Club River Oaks |
| TUE 9/16 | 3:00 PM | League | Thomaston | Lakeview | Crestbrook Park - Crestbrook Park Golf |
| TUE 9/16 | 3:00 PM | League | Norwalk | Trumbull | Oak Hills Golf Course - Oak Hills Golf Course |
| TUE 9/16 | 3:00 PM | League | Hall | Northwest Catholic | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 9/16 | 3:00 PM | League | Simsbury | Avon | Simsbury High School - Simsbury Farms CC |
| TUE 9/16 | 3:00 PM | League | Fairfield Ludlowe | Ridgefield | Smith Richardson Golf Course - Smith Richardson Golf Course |
| TUE 9/16 | 3:00 PM | League | Southington | Conard | Southington High School - Southington Country Club |
| TUE 9/16 | 3:00 PM | League | Berlin | Windsor | Timberlin Golf Course - Timberlin Golf Course |
| TUE 9/16 | 3:00 PM | League | Farmington | Lewis Mills | Tunxis Country Club - Tunxis Country Club |
| TUE 9/16 | 3:00 PM | League | Shepaug Valley | Northwestern | Washington Club Golf Course - Washington Club Golf Course |
| TUE 9/16 | 3:00 PM | League | Masuk | Stratford | Whitney Farms Golf Course - Whitney Farms Golf Course |
| TUE 9/16 | 3:10 PM | League | St. Joseph | Darien | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| TUE 9/16 | 3:15 PM | League | Wilton | Staples | Rolling Hills Country Club - Rolling Hills Country Club |
| WED 9/17 | 3:00 PM | League | New Milford | Newtown | Candlewood Valley Country Club - Candlewood Valley Country Club |
| WED 9/17 | 3:00 PM | League | Darien | Norwalk | Country Club of Darien - Country Club of Darien |
| WED 9/17 | 3:00 PM | League | Westhill | St. Joseph | EG Brennan Golf Course - E Gaynor Brennan Golf Course |
| WED 9/17 | 3:00 PM | League | Simsbury | Glastonbury, Newington | Hop Meadow Country Club - Hop Meadow Country Club |
| WED 9/17 | 3:00 PM | League | Brien McMahon | New Canaan | Oak Hills Golf Course - Oak Hills Golf Course |
| WED 9/17 | 3:00 PM | League | Pomperaug | Brookfield | Pomperaug High School - Highfield Country Club |
| WED 9/17 | 3:00 PM | League | Immaculate | Masuk | Ridgewood CC - Ridgewood CC |
| WED 9/17 | 3:00 PM | League | Fairfield Warde | Greenwich | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 9/17 | 3:00 PM | League | Wethersfield | Rocky Hill | Wethersfield Country Club - Wethersfield Country Club |
| WED 9/17 | 3:15 PM | Non-League | Trumbull | Fairfield Prep | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| THU 9/18 | 2:30 PM | League | Danbury | Brien McMahon | Richter Park Golf Course - Richter Park Golf Course |
| THU 9/18 | 3:00 PM | League | Bethel | Newtown | Bethel High School - Connecticut Country Club |
| THU 9/18 | 3:00 PM | League | Bunnell | Notre Dame Prep | Bunnell HS - Blackhawk Country Club (Old OCC) |
| THU 9/18 | 3:00 PM | League | Housatonic Regional | Lakeview | Canaan Country Club - Canaan Country Club |
| THU 9/18 | 3:00 PM | League | Thomaston | Gilbert | Crestbrook Park - Crestbrook Park Golf |
| THU 9/18 | 3:00 PM | League | Newington | Windsor, Wethersfield | Indian Hill Country Club - Indian Hill Country Club |
| THU 9/18 | 3:00 PM | League | Lewis Mills | Northwest Catholic | Lewis Mills High School - Fairview Farm Golf Course |
| THU 9/18 | 3:00 PM | League | Stratford | New Fairfield | Mill River Country Club - Mill River Country Club |
| THU 9/18 | 3:00 PM | League | Pomperaug | Masuk | Pomperaug High School - Highfield Country Club |
| THU 9/18 | 3:00 PM | League | Rocky Hill | Glastonbury | Rocky Hill High School - Stanley Golf Course |
| THU 9/18 | 3:00 PM | League | Fairfield Warde | Trumbull | Smith Richardson Golf Course - Smith Richardson Golf Course |
| THU 9/18 | 3:00 PM | League | Southington | Farmington | Southington High School - Southington Country Club |
| THU 9/18 | 3:00 PM | League | Avon | Hall | The Golf Club of Avon - The Golf Club of Avon |
| THU 9/18 | 3:00 PM | League | Berlin | New Britain | Timberlin Golf Course - Timberlin Golf Course |
| THU 9/18 | 3:00 PM | League | Shepaug Valley | Nonnewaug | Washington Club Golf Course - Washington Club Golf Course |
| THU 9/18 | 3:00 PM | Non-League | Ridgefield | Fairfield Prep | Ridgefield Golf Course - Ridgefield Golf Course |
| THU 9/18 | 3:15 PM | League | Wilton | Stamford | Rolling Hills Country Club - Rolling Hills Country Club |
| THU 9/18 | 3:30 PM | League | Staples | New Canaan | Longshore Golf Course - Longshore Golf Course |
| FRI 9/19 | 3:00 PM | League | Conard | Simsbury | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| MON 9/22 | 3:00 PM | League | Nonnewaug | Northwestern | Crestbrook Park - Crestbrook Park Golf |
| MON 9/22 | 3:00 PM | League | Gilbert | Housatonic Regional | Green woods Country Club - Green woods Country Club |
| MON 9/22 | 3:00 PM | League | Newington | Glastonbury | Indian Hill Country Club - Indian Hill Country Club |
| MON 9/22 | 3:00 PM | League | Windsor | Wethersfield, Avon | Keney Park Golf Course - Keney Park Golf Course |
| MON 9/22 | 3:00 PM | League | Lakeview | Shepaug Valley | Lakeview Regional High School - Litchfield Country Club (LCC) |
| MON 9/22 | 3:00 PM | League | Joel Barlow | Immaculate | Redding Country Club - Redding Country Club |
| MON 9/22 | 3:00 PM | League | Simsbury | Lewis Mills | Simsbury High School - Simsbury Farms CC |
| MON 9/22 | 3:00 PM | League | Brookfield | Bunnell | Sunset Hill Golf Course - Sunset Hill Golf Course |
| MON 9/22 | 3:00 PM | League | Darien | Staples | Wee Burn CC - Wee Burn CC |
| MON 9/22 | 3:00 PM | Non-League | Greenwich | Fairfield Prep | Round Hill Country Club - Round Hill Country Club |
| MON 9/22 | 3:30 PM | League | Newtown | Notre Dame Prep | Rock Ridge Country Club - Rock Ridge Country Club |
| TUE 9/23 | 3:00 PM | League | Housatonic Regional | Thomaston | Canaan Country Club - Canaan Country Club |
| TUE 9/23 | 3:00 PM | League | Windsor | Berlin | Goodwin Park Golf Course - Goodwin Park Golf Course |
| TUE 9/23 | 3:00 PM | League | Northwestern | Lakeview | Northwestern Regional H.S. - Norfolk CC |
| TUE 9/23 | 3:00 PM | League | Shepaug Valley | Gilbert | Washington Club Golf Course - Washington Club Golf Course |
| TUE 9/23 | 3:00 PM | Non-League | Immaculate | New Fairfield | Ridgewood CC - Ridgewood CC |
| WED 9/24 | 3:00 PM | League | New Milford | New Fairfield | Candlewood Valley Country Club - Candlewood Valley Country Club |
| WED 9/24 | 3:00 PM | League | Westhill | Darien | EG Brennan Golf Course - E Gaynor Brennan Golf Course |
| WED 9/24 | 3:00 PM | League | Brien McMahon | Ridgefield | Oak Hills Golf Course - Oak Hills Golf Course |
| WED 9/24 | 3:00 PM | League | Norwalk | St. Joseph | Oak Hills Golf Course - Oak Hills Golf Course |
| WED 9/24 | 3:00 PM | League | Pomperaug | Weston | Pomperaug High School - Highfield Country Club |
| WED 9/24 | 3:00 PM | League | Fairfield Ludlowe | Wilton | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 9/24 | 3:00 PM | League | Southington | Hall | Southington High School - Southington Country Club |
| WED 9/24 | 3:00 PM | League | Wethersfield | Northwest Catholic, Rocky Hill, Avon | Wethersfield Country Club - Wethersfield Country Club |
| WED 9/24 | 3:00 PM | League | Masuk | Joel Barlow | Whitney Farms Golf Course - Whitney Farms Golf Course |
| WED 9/24 | 3:00 PM | Non-League | Conard | Newington, Berlin | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| WED 9/24 | 3:15 PM | League | Trumbull | Staples | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 9/24 | 3:30 PM | League | New Canaan | Fairfield Warde | New Canaan HS - CCNC |
| WED 9/24 | 3:30 PM | Non-League | Fairfield Prep | Glastonbury | CC of Fairfield - CC of Fairfield |
| THU 9/25 | 3:00 PM | League | Avon | Northwest Catholic | The Golf Club of Avon - The Golf Club of Avon |
| THU 9/25 | 3:00 PM | League | Berlin | Newington | Timberlin Golf Course - Timberlin Golf Course |
| THU 9/25 | 3:10 PM | League | Greenwich | Westhill | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| THU 9/25 | Postponed | League | CIAC | Weston, Glastonbury, Pomperaug, Brookfield, Trumbull, Rocky Hill, Joel Barlow, Masuk, New Fairfield, Danbury, Fairfield Prep | [CIAC] Orange Hill GC - [CIAC] Orange Hill GC |
| THU 9/25 | Postponed | League | Stratford | Bunnell | Mill River Country Club - Mill River Country Club |
| FRI 9/26 | 3:30 PM | League | Gilbert | Northwestern | Green woods Country Club - Green woods Country Club |
| MON 9/29 | 3:00 PM | League | Brookfield | Bethel | Candlewood Valley Country Club - Candlewood Valley Country Club |
| MON 9/29 | 3:00 PM | League | New Fairfield | Joel Barlow | Club River Oaks - Club River Oaks |
| MON 9/29 | 3:00 PM | League | Nonnewaug | Gilbert | Crestbrook Park - Crestbrook Park Golf |
| MON 9/29 | 3:00 PM | League | Notre Dame Prep | Immaculate | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| MON 9/29 | 3:00 PM | League | Newington | Berlin, Conard, Glastonbury | Indian Hill Country Club - Indian Hill Country Club |
| MON 9/29 | 3:00 PM | League | Northwestern | Thomaston | Northwestern Regional H.S. - Norfolk CC |
| MON 9/29 | 3:00 PM | League | Pomperaug | Newtown | Pomperaug High School - Highfield Country Club |
| MON 9/29 | 3:00 PM | League | Hall | Simsbury | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| MON 9/29 | 3:00 PM | League | Shepaug Valley | Housatonic Regional | Washington Club Golf Course - Washington Club Golf Course |
| MON 9/29 | 3:00 PM | League | Darien | Trumbull | Wee Burn CC - Wee Burn CC |
| MON 9/29 | 3:15 PM | League | Staples | Fairfield Ludlowe | Longshore Golf Course - Longshore Golf Course |
| MON 9/29 | 3:15 PM | Non-League | Weston | Masuk | Weston High School - Aspetuck Country Club |
| TUE 9/30 | 10:00 AM | Non-League | Avon | Joel Barlow, Northwest Catholic, Simsbury, Newtown, Lewis Mills, Masuk, New Milford, Farmington, Berlin, Conard, Hall, Brookfield, Weston, Pomperaug, Southington, Wethersfield, Glastonbury | Hop Meadow Country Club - Hop Meadow Country Club |
| TUE 9/30 | 2:30 PM | League | Danbury | Fairfield Ludlowe | Richter Park Golf Course - Richter Park Golf Course |
| TUE 9/30 | 3:00 PM | League | New Fairfield | Bethel | Club River Oaks - Club River Oaks |
| TUE 9/30 | 3:00 PM | League | Thomaston | Nonnewaug | Crestbrook Park - Crestbrook Park Golf |
| TUE 9/30 | 3:00 PM | League | Westhill | Brien McMahon | EG Brennan Golf Course - E Gaynor Brennan Golf Course |
| TUE 9/30 | 3:00 PM | League | Northwestern | Housatonic Regional | Northwestern Regional H.S. - Norfolk CC |
| TUE 9/30 | 3:00 PM | League | Norwalk | Stamford | Oak Hills Golf Course - Oak Hills Golf Course |
| TUE 9/30 | 3:00 PM | League | Immaculate | Bunnell | Richter Park Golf Course - Richter Park Golf Course |
| TUE 9/30 | 3:00 PM | League | Ridgefield | Fairfield Warde | Ridgefield Golf Course - Ridgefield Golf Course |
| TUE 9/30 | 3:10 PM | League | Greenwich | Staples | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| TUE 9/30 | 3:10 PM | League | St. Joseph | New Canaan | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 10/1 | 3:00 PM | League | Bethel | Masuk | Bethel High School - Connecticut Country Club |
| WED 10/1 | 3:00 PM | League | Fairfield Prep | Joel Barlow | CC of Fairfield - CC of Fairfield |
| WED 10/1 | 3:00 PM | League | Thomaston | Shepaug Valley | Crestbrook Park - Crestbrook Park Golf |
| WED 10/1 | 3:00 PM | League | Notre Dame Prep | Weston | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| WED 10/1 | 3:00 PM | League | Windsor | Glastonbury | Keney Park Golf Course - Keney Park Golf Course |
| WED 10/1 | 3:00 PM | League | Lakeview | Nonnewaug | Lakeview Regional High School - Litchfield Country Club (LCC) |
| WED 10/1 | 3:00 PM | League | Conard | Northwest Catholic | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| WED 10/1 | 3:00 PM | League | New Britain | Wethersfield | Stanley Golf Course - Stanley Golf Course |
| WED 10/1 | 3:00 PM | League | Berlin | Southington, Rocky Hill | Timberlin Golf Course - Timberlin Golf Course |
| WED 10/1 | 3:00 PM | League | Farmington | Avon | Tunxis Country Club - Tunxis Country Club |
| WED 10/1 | 3:00 PM | League | Darien | Stamford | Woodway Country Club - Woodway Country Club |
| WED 10/1 | 3:15 PM | League | Trumbull | Danbury | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 10/1 | 3:30 PM | League | Newtown | Brookfield | Rock Ridge Country Club - Rock Ridge Country Club |
| THU 10/2 | 3:00 PM | League | Notre Dame Prep | New Milford | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| THU 10/2 | 3:00 PM | League | Newington | Southington | Indian Hill Country Club - Indian Hill Country Club |
| THU 10/2 | 3:00 PM | League | Lakeview | Thomaston | Lakeview Regional High School - Litchfield Country Club (LCC) |
| THU 10/2 | 3:00 PM | League | Northwestern | Shepaug Valley | Northwestern Regional H.S. - Norfolk CC |
| THU 10/2 | 3:00 PM | League | New Britain | Rocky Hill | Stanley Golf Course - Stanley Golf Course |
| THU 10/2 | 3:00 PM | Non-League | Berlin | Fairfield Prep | Timberlin Golf Course - Timberlin Golf Course |
| MON 10/6 | 3:00 PM | League | New Milford | Stratford | Candlewood Valley Country Club - Candlewood Valley Country Club |
| MON 10/6 | 3:00 PM | League | New Fairfield | Immaculate | Club River Oaks - Club River Oaks |
| MON 10/6 | 3:00 PM | League | Nonnewaug | Housatonic Regional | Crestbrook Park - Crestbrook Park Golf |
| MON 10/6 | 3:00 PM | League | Glastonbury | Wethersfield | Glastonbury Hills Country Club - Glastonbury Hills Country Club |
| MON 10/6 | 3:00 PM | League | Pomperaug | Notre Dame Prep | Pomperaug High School - Highfield Country Club |
| MON 10/6 | 3:00 PM | League | New Britain | Rocky Hill | Stanley Golf Course - Stanley Golf Course |
| MON 10/6 | 3:00 PM | League | Farmington | Conard | Tunxis Country Club - Tunxis Country Club |
| MON 10/6 | 3:00 PM | Non-League | Lewis Mills | Lakeview, Northwestern | Lewis Mills High School - Fairview Farm Golf Course |
| MON 10/6 | 3:15 PM | League | Staples | St. Joseph | Longshore Golf Course - Longshore Golf Course |
| MON 10/6 | 3:15 PM | League | Wilton | Trumbull | Rolling Hills Country Club - Rolling Hills Country Club |
| TUE 10/7 | 3:00 PM | League | Brookfield | New Milford | Candlewood Valley Country Club - Candlewood Valley Country Club |
| TUE 10/7 | 3:00 PM | League | Fairfield Prep | Greenwich | Great River Golf Course - Great River Golf Course |
| TUE 10/7 | 3:00 PM | League | Lewis Mills | Conard | Lewis Mills High School - Fairview Farm Golf Course |
| TUE 10/7 | 3:00 PM | League | Stratford | Pomperaug | Mill River Country Club - Mill River Country Club |
| TUE 10/7 | 3:00 PM | League | Ridgefield | Trumbull | Ridgefield Golf Course - Ridgefield Golf Course |
| TUE 10/7 | 3:00 PM | League | Hall | Farmington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 10/7 | 3:00 PM | League | Rocky Hill | Windsor | Rocky Hill High School - Stanley Golf Course |
| TUE 10/7 | 3:00 PM | League | Fairfield Warde | Stamford | Smith Richardson Golf Course - Smith Richardson Golf Course |
| TUE 10/7 | 3:00 PM | League | Southington | Avon | Southington High School - Southington Country Club |
| TUE 10/7 | 3:00 PM | League | Northwest Catholic | Simsbury | Wampanoag Country Club - Wampanoag Country Club |
| TUE 10/7 | 3:00 PM | League | Wethersfield | Berlin | Wethersfield Country Club - Wethersfield Country Club |
| TUE 10/7 | 3:10 PM | League | St. Joseph | Danbury | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| TUE 10/7 | 3:15 PM | League | Wilton | Westhill | Rolling Hills Country Club - Rolling Hills Country Club |
| TUE 10/7 | 3:15 PM | League | Weston | Bethel | Weston High School - Aspetuck Country Club |
| TUE 10/7 | 3:30 PM | League | Newtown | Masuk | Rock Ridge Country Club - Rock Ridge Country Club |
| WED 10/8 | 12:30 PM | League | Stamford | Westhill | Stamford High - Woodway Country Club |
| WED 10/8 | 3:00 PM | League | Bethel | Immaculate | Bethel High School - Connecticut Country Club |
| WED 10/8 | 3:00 PM | League | New Milford | Joel Barlow | Candlewood Valley Country Club - Candlewood Valley Country Club |
| WED 10/8 | 3:00 PM | League | Notre Dame Prep | Stratford | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| WED 10/8 | 3:00 PM | League | Gilbert | Lakeview | Green woods Country Club - Green woods Country Club |
| WED 10/8 | 3:00 PM | League | Newington | Hall | Indian Hill Country Club - Indian Hill Country Club |
| WED 10/8 | 3:00 PM | League | Windsor | Wethersfield | Keney Park Golf Course - Keney Park Golf Course |
| WED 10/8 | 3:00 PM | League | Rocky Hill | Berlin | Rocky Hill High School - Stanley Golf Course |
| WED 10/8 | 3:00 PM | League | Fairfield Ludlowe | New Canaan | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 10/8 | 3:00 PM | League | Farmington | Southington | Tunxis Country Club - Tunxis Country Club |
| WED 10/8 | 3:00 PM | Non-League | Darien | Fairfield Prep | Woodway Country Club - Woodway Country Club |
| WED 10/8 | 3:10 PM | League | St. Joseph | Brien McMahon | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 10/8 | 3:15 PM | League | Wilton | Fairfield Warde | Rolling Hills Country Club - Rolling Hills Country Club |
| WED 10/8 | 3:15 PM | League | Weston | Brookfield | Weston High School - Aspetuck Country Club |
| THU 10/9 | 3:00 PM | League | Bethel | Bunnell | Bethel High School - Connecticut Country Club |
| THU 10/9 | 3:00 PM | League | Glastonbury | Berlin | Glastonbury Hills Country Club - Glastonbury Hills Country Club |
| THU 10/9 | 3:00 PM | League | Lewis Mills | Hall | Lewis Mills High School - Fairview Farm Golf Course |
| THU 10/9 | 3:00 PM | League | Conard | Avon | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 10/9 | 3:00 PM | League | Southington | Simsbury | Southington High School - Southington Country Club |
| THU 10/9 | 3:00 PM | League | Northwest Catholic | Farmington | Wampanoag Country Club - Wampanoag Country Club |
| THU 10/9 | 3:00 PM | Non-League | Shepaug Valley | Brookfield | Lake Waramaug Country Club - Lake Waramaug Country Club |
| TUE 10/14 | 12:01 AM | Postseason | Darien | | Wee Burn CC - Wee Burn CC |
| TUE 10/14 | 3:00 PM | League | Avon | Lewis Mills | Blue Fox Run Golf Course - Blue Fox Run Golf Course |
| TUE 10/14 | 3:00 PM | League | Hall | Conard | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 10/14 | 3:00 PM | League | Rocky Hill | Newington | Rocky Hill High School - Stanley Golf Course |
| TUE 10/14 | 3:00 PM | League | Simsbury | Farmington | Simsbury High School - Simsbury Farms CC |
| TUE 10/14 | 3:00 PM | League | Southington | Northwest Catholic | Southington High School - Southington Country Club |
| TUE 10/14 | 3:00 PM | League | New Britain | Windsor, Newington | Stanley Golf Course - Stanley Golf Course |
| TUE 10/14 | 8:00 AM | Postseason | Lakeview | Thomaston, Shepaug Valley, Northwestern, Gilbert, Nonnewaug, Housatonic Regional | Fairfiew Farm Golf Course - Fairfiew Farm Golf Course |
| WED 10/15 | 2:30 PM | League | Ridgefield | Wilton | Ridgefield Golf Course - Ridgefield Golf Course |
| WED 10/15 | 3:00 PM | League | Lewis Mills | Southington | Lewis Mills High School - Fairview Farm Golf Course |
| WED 10/15 | 3:00 PM | League | Brien McMahon | Norwalk | Shorehaven Golf Club - Shorehaven Golf Club |
| WED 10/15 | 3:00 PM | Non-League | Fairfield Warde | Fairfield Prep, Fairfield Ludlowe | CC of Fairfield - CC of Fairfield |
| WED 10/15 | 3:15 PM | League | Trumbull | Westhill | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 10/15 | Canceled | League | Fairfield Prep | Fairfield Ludlowe | CC of Fairfield - CC of Fairfield |
| THU 10/16 | 10:00 AM | Postseason | Central Connecticut Conference (CCC) | Lewis Mills, Farmington, Conard, Berlin, Avon, New Britain, Newington, Rocky Hill, Northwest Catholic, Simsbury, Southington, Glastonbury, Wethersfield, Windsor, Hall | Stanley Golf Course - Stanley Golf Course |