| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 12/16 | 7:00 p.m. | Varsity | League | Normal | Home | Branford | Loss | 52-59 | | Fred Kelly Gymnasium | |
| TUE 12/20 | 7:00 p.m. | Varsity | League | Normal | Away | Guilford | Loss | 33-61 | | Main Gym at GHS | |
| TUE 12/27 | TBA | Varsity | League | Normal | Home | TwoRiversMagnet | Win | 63-19 | | Fred Kelly Gymnasium | |
| THU 12/29 | 5:00 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 33-58 | | Fred Kelly Gymnasium | |
| TUE 1/3 | 7:00 p.m. | Varsity | League | Normal | Away | Branford | Loss | 40-60 | | James L MacVeigh Alumni Athletic Complex - Gym | |
| WED 1/4 | 7:00 p.m. | Varsity | League | Normal | Home | Guilford | Loss | 24-68 | | Fred Kelly Gymnasium | |
| FRI 1/6 | 7:00 p.m. | Varsity | League | Normal | Away | WestHaven | Loss | 32-63 | | WHHS Gym | |
| MON 1/9 | 7:00 p.m. | Varsity | League | Normal | Home | WilburCross | Loss | 39-66 | | Fred Kelly Gymnasium | |
| WED 1/11 | 7:00 p.m. | Varsity | League | Normal | Away | DanielHand | Loss | 14-68 | | DHHS Gym | |
| FRI 1/13 | 7:00 p.m. | Varsity | League | Normal | Home | LymanHall | Loss | 28-51 | | Fred Kelly Gymnasium | |
| TUE 1/17 | 7:00 p.m. | Varsity | League | Normal | Away | JamesHillhouse | Loss | 24-57 | | Hillhouse HS Gym | |
| THU 1/19 | 7:00 p.m. | Varsity | League | Normal | Away | JonathanLaw | Loss | 31-64 | | Jonathan Law HS-Richetelli Gymnasium | |
| SAT 1/21 | 3:00 p.m. | Varsity | League | Normal | Away | CoginchaugReg | Win | 57-53 | | Maynard Stender Gymnasium @ CRHS | |
| FRI 1/27 | 7:00 p.m. | Varsity | League | Normal | Home | WestHaven | Loss | 48-61 | | Fred Kelly Gymnasium | |
| MON 1/30 | 7:00 p.m. | Varsity | League | Normal | Away | WilburCross | Loss | 39-57 | | Wilbur Cross Gym | |
| WED 2/1 | 7:00 p.m. | Varsity | League | Normal | Home | DanielHand | Loss | 17-61 | | Fred Kelly Gymnasium | |
| FRI 2/3 | 7:00 p.m. | Varsity | League | Normal | Away | LymanHall | Loss | 39-56 | | Lyman Hall High School Gymnasium | |
| MON 2/6 | 7:00 p.m. | Varsity | League | Normal | Away | Maloney | Loss | 41-49 | | Maloney High School | |
| TUE 2/7 | 7:00 p.m. | Varsity | League | Normal | Home | JamesHillhouse | Loss | 42-61 | | Fred Kelly Gymnasium | |
| SAT 2/11 | 3:00 p.m. | Varsity | League | Normal | Home | JonathanLaw | Loss | 41-71 | | Fred Kelly Gymnasium | |