| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 12/13 | 6:00 PM | Varsity | League | Normal | Home | Fairfield Warde | | | | Westhill High School - New Gym | |
| SAT 12/16 | 9:00 AM | Varsity | League | Normal | Away | Enfield | | | | Fairfield Ludlowe High School - Main Gym | |
| Brien McMahon | | |
| Fairfield Prep | | |
| Bethel | | |
| Pomperaug | | |
| Stratford | | |
| Branford | | |
| Fairfield Ludlowe | | |
| Stamford | | |
| Joel Barlow | | |
| Norwalk | | |
| St. Joseph | | |
| WED 12/20 | 5:00 PM | Varsity | League | Normal | Away | Darien | | | | Darien High School - DHS South Gym | |
| SAT 12/23 | 9:00 AM | Varsity | League | Normal | Away | Brookfield/Shepaug | | | | Trumbull High School - THS Main Gym | |
| Ridgefield | | |
| Conard | | |
| Trumbull | | |
| Staples | | |
| FRI 12/29 | 9:00 AM | Varsity | Non-League | Normal | Away | New Britain | | | | Glastonbury High School - Gym | |
| Daniel Hand | | |
| Lyman Memorial - Windham Tech | | |
| Newington | | |
| Hall | | |
| Glastonbury | | |
| WED 1/3 | 6:00 PM | Varsity | League | Normal | Home | Brien McMahon | | | | Westhill High School - New Gym | |
| WED 1/10 | 6:00 PM | Varsity | League | Normal | Away | Stamford | | | | Stamford High School - Kuczo Gymnasium | |
| SAT 1/13 | 8:45 AM | Varsity | League | Normal | Away | Northwestern | | | | Staples High School - Staples Gym | |
| Simsbury | | |
| Maloney | | |
| Staples | | |
| Foran | | |
| Fairfield Prep | | |
| Stratford | | |
| Guilford | | |
| SAT 1/20 | 9:00 AM | Varsity | Non-League | Normal | Away | South Windsor | | | | Conard High School - Main Gym | |
| Fairfield Ludlowe | | |
| New Fairfield | | |
| Brien McMahon | | |
| Conard | | |
| WED 1/24 | 6:00 PM | Varsity | League | Normal | Home | Danbury | | | | Westhill High School - New Gym | |
| SAT 1/27 | 9:30 AM | Varsity | Tournament | Normal | Away | Masuk | | | | Brookfield High School - BHS Small & Big Gym | |
| Brookfield/Shepaug | | |
| Darien | | |
| Joel Barlow | | |
| Pomperaug | | |
| Derby/Oxford/Holy Cross | | |
| Stamford | | |
| Danbury | | |
| Wilton | | |
| Shelton | | |
| St. Joseph | | |
| Jonathan Law | | |
| New Canaan | | |
| WED 1/31 | 6:00 PM | Varsity | League | Normal | Away | Greenwich | | | | Greenwich High School - Gymnasium | |
| SAT 2/3 | 10:00 AM | Varsity | Tournament | Normal | Away | Daniel Hand | | | | Waterford High School - Francis X. Sweeney Field House | |
| St. Paul Catholic | | |
| Waterford | | |
| Ledyard | | |
| Windham | | |
| TUE 2/6 | 6:00 PM | Varsity | League | Normal | Home | Norwalk | | | | Westhill High School - New Gym | |
| FRI 2/9 | 4:30 PM | Varsity | Tournament | Normal | Away | Darien | | | | New Canaan HS - Main Gym | |
| | |
| Staples | | |
| New Canaan | | |
| Stamford | | |
| Greenwich | | |
| Ridgefield | | |
| Fairfield Ludlowe | | |
| Trumbull | | |
| Brien McMahon | | |
| Wilton | | |
| Danbury | | |
| Fairfield Warde | | |
| St. Joseph | | |
| Norwalk | | |