| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 8/21 | 12:00 PM | Varsity | Non-League | Normal | Home | Northwestern | | 186-200 | | Lakeview High School - Litchfield Country Club (LCC) | |
| WED 8/28 | 3:30 PM | Varsity | Non-League | Normal | Home | Housatonic Regional | | 163-202 | | Lakeview High School - Litchfield Country Club (LCC) | |
| TUE 9/3 | 3:00 PM | Varsity | League | Normal | Home | Northwestern | | 189-190 | | Lakeview High School - Litchfield Country Club (LCC) | |
| THU 9/5 | 3:30 PM | Varsity | League | Normal | Home | Housatonic Regional | | 187-217 | | Lakeview High School - Litchfield Country Club (LCC) | |
| MON 9/9 | 3:00 PM | Varsity | League | Normal | Home | Nonnewaug | | 191-192 | | Lakeview High School - Litchfield Country Club (LCC) | |
| THU 9/12 | 3:00 PM | Varsity | League | Normal | Home | Shepaug Valley | | 180-174 | | Lakeview High School - Litchfield Country Club (LCC) | |
| MON 9/16 | 4:00 PM | Varsity | League | Normal | Away | Gilbert | | | | Green woods Country Club - Green woods Country Club | 2:45 PM - 1 Bus |
| THU 9/19 | Postponed | Varsity | League | Postponed | Away | Northwestern | | | | Northwestern Regional H.S. - Norfolk CC | 2:30 PM - 1 Bus |
| MON 9/23 | 3:30 PM | Varsity | League | Normal | Away | Housatonic Regional | | | | Canaan Country Club - Canaan Country Club | |
| WED 9/25 | 3:30 PM | Varsity | League | Normal | Away | Nonnewaug | | | | Crestbrook Park - Crestbrook Park Golf | 2:30 PM - 1 Bus |
| THU 9/26 | 3:00 PM | Varsity | Non-League | Normal | Away | Immaculate | | | | [CIAC] Orange Hill GC - [CIAC] Orange Hill GC | 1:30 PM - 1 Bus |
| Joel Barlow | | |
| Brookfield | | |
| Danbury | | |
| Fairfield Prep | | |
| New Fairfield | | |
| Pomperaug | | |
| Rocky Hill | | |
| Shepaug Valley | | |
| Trumbull | | |
| Weston | | |
| CIAC | | |
| MON 9/30 | 3:30 PM | Varsity | League | Normal | Away | Shepaug Valley | | | | Washington Club Golf Course - Washington Club Golf Course | 2:30 PM - 1 Bus |
| WED 10/2 | 3:30 PM | Varsity | Non-League | Normal | Away | Lewis Mills | | | | Lewis Mills High School - Fairview Farm Golf Course | 2:30 PM - 1 Bus |
| THU 10/3 | 3:00 PM | Varsity | League | Normal | Home | Gilbert | | | | Lakeview High School - Litchfield Country Club (LCC) | |
| TUE 10/15 | 8:00 AM | Varsity | League | Normal | Away | | | | | Fairfiew Farm Golf Course - Fairfiew Farm Golf Course | 2:30 PM - 1 Bus |
| Gilbert | | |
| Nonnewaug | | |
| Housatonic Regional | | |
| Shepaug Valley | | |
| Northwestern | | |
| TUE 10/22 | 12:01 AM | Varsity | Postseason | Normal | Away | | | | | Not Listed - Stanley Golf Course - New Britain | 2:30 PM - 1 Bus |