| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 12/9 | 8:00 AM | Varsity | Scrimmage | Normal | Home | Bunnell | | | | Staples High School - Field House | |
| Shelton | | |
| WED 12/13 | 7:00 PM | Varsity | League | Normal | Home | Norwalk | | | | Staples High School - Field House | |
| THU 12/21 | 6:00 PM | Varsity | League | Normal | Away | Brien McMahon | | | | Brien McMahon High School - Kehoe - King Gymnasium | 4:30 PM |
| SAT 12/23 | 9:00 AM | Varsity | League | Normal | Away | Westhill | | | | Trumbull High School - THS Main Gym | 7:15 AM |
| Conard | | |
| Ridgefield | | |
| Trumbull | | |
| Brookfield/Shepaug | | |
| WED 12/27 | 9:30 PM | Varsity | League | Normal | Away | Bloomfield Weaver | | | | Simsbury High School - Gym 2 | 6:00 AM |
| Somers | | |
| | |
| | |
| Simsbury | | |
| East Hartford | | |
| Middletown | | |
| | |
| | |
| Jonathan Law | | |
| FRI 12/29 | 8:30 AM | Varsity | League | Normal | Away | Wethersfield | | | | Bristol Central High School - Charles C. Marsh Gymnasium | 6:30 AM |
| Conard | | |
| Bristol Central | | |
| WED 1/3 | 6:00 PM | Varsity | League | Normal | Home | Wilton | | | | Staples High School - Field House | |
| SAT 1/6 | 9:00 AM | Varsity | League | Normal | Away | Middletown | | | | Bristol Central High School - Charles C. Marsh Gymnasium | 5:45 AM - JV/V going together |
| East Hartford | | |
| Wethersfield | | |
| Hall | | |
| Berlin | | |
| Farmington | | |
| Bristol Central | | |
| Terryville-Thomaston | | |
| Ledyard | | |
| Guilford | | |
| Bristol Eastern | | |
| New Fairfield | | |
| New Milford | | |
| Plainville | | |
| Enfield | | |
| Avon | | |
| Pomperaug | | |
| WED 1/10 | 7:00 PM | Varsity | League | Normal | Away | New Canaan | | | | New Canaan HS - Main Gym | 5:15 PM |
| SAT 1/13 | 8:45 AM | Varsity | League | Normal | Home | Simsbury | | | | Staples High School - Staples Gym | |
| Maloney | | |
| Northwestern | | |
| Foran | | |
| Fairfield Prep | | |
| Stratford | | |
| Westhill | | |
| Guilford | | |
| WED 1/17 | 6:00 PM | Varsity | League | Normal | Home | Fairfield Ludlowe | | | | Staples High School - Field House | |
| SAT 1/20 | 10:00 AM | Varsity | Non-League | Normal | Away | Jonathan Law | | | | Norwich Free Academy - Alumni Gym | 7:00 AM |
| Ledyard | | |
| Norwich Free Academy | | |
| Ellis Tech | | |
| Notre Dame-West Haven | | |
| Bristol Central | | |
| | |
| WED 1/24 | 5:00 PM | Varsity | League | Normal | Away | Darien | | | | Darien High School - DHS South Gym | 3:15 PM |
| WED 1/31 | 3:00 PM | Varsity | League | Normal | Away | St. Joseph | | | | St. Joseph High School - Gym | 1:30 PM |
| TUE 2/6 | 6:30 PM | Varsity | League | Normal | Home | Fairfield Warde | | | | Staples High School - Field House | |
| FRI 2/9 | 4:30 PM | Varsity | Tournament | Normal | Away | Wilton | | | | New Canaan HS - Main Gym | 2:15 PM |
| Norwalk | | |
| Darien | | |
| Trumbull | | |
| Greenwich | | |
| St. Joseph | | |
| New Canaan | | |
| Fairfield Warde | | |
| Ridgefield | | |
| Brien McMahon | | |
| | |
| Stamford | | |
| Westhill | | |
| Danbury | | |
| Fairfield Ludlowe | | |