| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 12/18 | 7:00 p.m. | Varsity | League | Normal | Home | OHPlatt | Win | 56-38 | | Cheshire High School-Gym West | |
| FRI 12/20 | 7:00 p.m. | Varsity | League | Normal | Away | JosephForan | Loss | 34-37 | | Foran High School -Edna L. Fraser Gymnasium | |
| FRI 12/27 | 2:00 p.m. | Varsity | League | Normal | Away | OHPlatt | Win | 51-30 | | Platt High School-Gym | |
| MON 12/30 | 5:30 p.m. | Varsity | League | Normal | Away | Plainville | Loss | 34-39 | | Plainville High School-Wood Gymnasium | |
| FRI 1/3 | 6:00 p.m. | Varsity | League | Normal | Away | WestHaven | Loss | 43-49 | | West Haven High School-Gym | |
| TUE 1/7 | 5:15 p.m. | Varsity | League | Normal | Home | WilburCross | Loss | 37-53 | | Cheshire High School-Gym West | |
| FRI 1/10 | 7:00 p.m. | Varsity | League | Normal | Home | Shelton | Loss | 20-45 | | Cheshire High School-Gym - East | |
| MON 1/13 | 5:15 p.m. | Varsity | League | Normal | Home | DanielHand | Loss | 29-51 | | Cheshire High School-Gym West | |
| WED 1/15 | 6:15 p.m. | Varsity | League | Normal | Away | AcademyofOurLadyofMercy | Win | 49-32 | | Lauralton Hall-Gym | |
| FRI 1/17 | 7:00 p.m. | Varsity | League | Normal | Home | JosephForan | Loss | 33-39 | | Cheshire High School-Gym West | |
| TUE 1/21 | 7:00 p.m. | Varsity | League | Normal | Home | LymanHall | Loss | 44-63 | | Cheshire High School-Gym - East | |
| FRI 1/24 | 6:00 p.m. | Varsity | League | Normal | Home | WestHaven | Loss | 45-64 | | Cheshire High School-Gym West | |
| TUE 1/28 | 7:00 p.m. | Varsity | League | Normal | Away | Branford | Loss | 46-54 | | Branford High School-Gym | |
| FRI 1/31 | 7:00 p.m. | Varsity | League | Normal | Away | WilburCross | Loss | 39-51 | | Wilbur Cross High School-Gym | |
| MON 2/3 | 7:00 p.m. | Varsity | League | Normal | Away | Shelton | Loss | 33-54 | | Shelton High School-High School - Murray Gymnasium | |
| WED 2/5 | 7:00 p.m. | Varsity | League | Normal | Away | DanielHand | Loss | 41-63 | | Daniel Hand HS-DHHS Gym | |
| FRI 2/7 | 6:00 p.m. | Varsity | League | Normal | Home | AcademyofOurLadyofMercy | Loss | 18-36 | | Cheshire High School-Gym - East | |
| WED 2/12 | 7:00 p.m. | Varsity | League | Normal | Away | LymanHall | Win | 37-34 | | Lyman Hall High School-Gymnasium | |
| FRI 2/14 | 6:00 p.m. | Varsity | League | Normal | Home | Branford | Win | 40-33 | | Cheshire High School-Gym West | |
| MON 2/17 | 6:00 p.m. | Varsity | League | Normal | Home | NorthHaven | Win | 47-42 OT | | Cheshire High School-Gym West | |