| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 12/13 | 5:30 p.m. | Varsity | League | Normal | Away | Bassick | Win | 54-7 | | Bassick High School-Gym | |
| THU 12/16 | 5:30 p.m. | Varsity | League | Normal | Away | Newtown | Loss | 18-38 | | Newtown High School-Gym | |
| THU 12/30 | 4:00 p.m. | Varsity | League | Normal | Away | NewCanaan | Loss | 19-29 | | New Canaan High School-Main Gym | |
| TUE 1/4 | 5:30 p.m. | Varsity | League | Normal | Away | Staples | Loss | 28-30 | | Staples High School-Staples Gym | |
| SAT 1/8 | 11:00 a.m. | Varsity | League | Normal | Home | Norwalk | Loss | 29-45 | | Darien High School-DHS Main Gym | |
| SAT 1/15 | 1:00 p.m. | Varsity | League | Normal | Away | Southington | Loss | 45-23 | | Southington High School-Gym West | |
| MON 1/17 | 1:30 p.m. | Varsity | League | Normal | Home | FairfieldLudlowe | Loss | 51-25 | | Darien High School-DHS Main Gym | |
| FRI 1/21 | 5:30 p.m. | Varsity | League | Normal | Away | Trumbull | Loss | 54-21 | | Trumbull High School-THS Main Gym | |
| SAT 1/22 | 11:45 a.m. | Varsity | League | Normal | Away | BrienMcMahon | Win | 33-17 | | Brien McMahon High School-Kehoe - King Gymnasium | |
| MON 1/24 | 5:15 p.m. | Varsity | League | Normal | Home | BridgeportCentral | Win | 55-24 | | Darien High School-DHS Main Gym | |
| THU 1/27 | 7:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 34-24 | | Fairfield Warde HS-Large Gym | |
| TUE 2/1 | 6:00 p.m. | Varsity | League | Normal | Away | Greenwich | Loss | 42-36 | | Greenwich High School-Gymnasium | |
| THU 2/3 | 6:00 p.m. | Varsity | League | Normal | Away | Westhill | Loss | 40-43 | | Westhill High School-Main Gym | |
| SAT 2/5 | 1:00 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 42-25 | | Darien High School-DHS Main Gym | |
| MON 2/7 | 5:30 p.m. | Varsity | League | Normal | Home | Danbury | Loss | 43-37 | | Darien High School-DHS Main Gym | |
| TUE 2/8 | 5:30 p.m. | Varsity | League | Normal | Home | StJoseph | Loss | 28-45 | | Darien High School-DHS Main Gym | |
| FRI 2/11 | 5:30 p.m. | Varsity | League | Normal | Home | NewCanaan | Win | 29-27 | | Darien High School-DHS Main Gym | |
| SAT 2/12 | 12:30 p.m. | Varsity | League | Normal | Home | WilburCross | Win | 43-39 | | Darien High School-DHS Main Gym | |
| MON 2/14 | 7:00 p.m. | Varsity | League | Normal | Away | Ridgefield | Loss | 39-15 | | Ridgefield High School-Main Gym | |
| WED 2/16 | 5:30 p.m. | Varsity | League | Normal | Home | Stamford | Loss | 49-36 | | Darien High School-DHS Main Gym | |