| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 12/13 | 5:30 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | | | | Fairfield Ludlowe High School - Aux Gym | 3:30 PM |
| SAT 12/16 | 9:00 AM | Varsity | League | Normal | Away | Norwalk | | | | Fairfield Ludlowe High School - Main Gym | 7:00 AM |
| Fairfield Prep | | |
| Bethel | | |
| Branford | | |
| Enfield | | |
| Fairfield Ludlowe | | |
| Joel Barlow | | |
| Brien McMahon | | |
| Pomperaug | | |
| St. Joseph | | |
| Stratford | | |
| Westhill | | |
| WED 12/20 | 6:00 PM | Varsity | League | Normal | Home | St. Joseph | | | | Stamford High School - SHS Aux Gym | |
| SAT 12/23 | 9:00 AM | Varsity | League | Normal | Away | North Haven | | | | Wilton HS - Nicholas Zeoli Fieldhouse | 7:00 AM |
| New Canaan | | |
| Wilton | | |
| WED 1/3 | 4:30 PM | Varsity | League | Normal | Away | Danbury | | | | Danbury High School - New gym | 2:30 PM |
| WED 1/10 | 6:00 PM | Varsity | League | Normal | Home | Westhill | | | | Stamford High School - Kuczo Gymnasium | |
| THU 1/18 | 6:00 PM | Varsity | League | Normal | Home | Norwalk | | | | Stamford High School - Kuczo Gymnasium | |
| WED 1/24 | 7:00 PM | Varsity | League | Normal | Home | Greenwich | | | | Stamford High School - Kuczo Gymnasium | |
| SAT 1/27 | 9:30 AM | Varsity | Tournament | Normal | Away | Brookfield/Shepaug | | | | Brookfield High School - BHS Small & Big Gym | 6:30 AM |
| Pomperaug | | |
| Danbury | | |
| St. Joseph | | |
| Darien | | |
| New Canaan | | |
| Masuk | | |
| Derby/Oxford/Holy Cross | | |
| Wilton | | |
| Joel Barlow | | |
| Shelton | | |
| Westhill | | |
| Jonathan Law | | |
| WED 1/31 | 6:00 PM | Varsity | League | Normal | Away | Trumbull | | | | Trumbull High School - Aux Gym | 3:45 PM |
| WED 2/7 | 6:00 PM | Varsity | League | Normal | Away | Brien McMahon | | | | Brien McMahon High School - Kehoe - King Gymnasium | 4:15 PM |
| FRI 2/9 | 4:30 PM | Varsity | Tournament | Normal | Away | Wilton | | | | New Canaan HS - Main Gym | 2:45 PM |
| New Canaan | | |
| Danbury | | |
| Greenwich | | |
| Darien | | |
| Brien McMahon | | |
| Trumbull | | |
| Ridgefield | | |
| Norwalk | | |
| Fairfield Ludlowe | | |
| Staples | | |
| Fairfield Warde | | |
| | |
| St. Joseph | | |
| Westhill | | |