| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 12/19 | 7:00 p.m. | Varsity | League | Normal | Away | Bunnell | Loss | 49-54 | | Bunnell High School-Bunnell Main Gym | |
| FRI 12/20 | 5:00 p.m. | Varsity | League | Normal | Home | WarrenHarding | Loss | 61-70 | | Bunnell High School-Bunnell Main Gym | |
| FRI 1/3 | 7:00 p.m. | Varsity | League | Normal | Away | Danbury | Loss | 51-70 | | Danbury High School-Main Gym | |
| TUE 1/7 | 7:00 p.m. | Varsity | League | Normal | Away | Trumbull | Loss | 56-69 | | Trumbull High School-THS Main Gym | |
| FRI 1/10 | 7:00 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 73-79 | | Darien High School-DHS Main Gym | |
| SAT 1/11 | 7:00 p.m. | Varsity | League | Normal | Away | Weston | Loss | 43-65 | | Weston High School-Gym (New) | |
| TUE 1/14 | 7:00 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 62-93 | | Darien High School-DHS Main Gym | |
| FRI 1/17 | 7:00 p.m. | Varsity | League | Normal | Away | BrienMcMahon | Loss | 65-79 | | Brien McMahon High School-Kehoe - King Gymnasium | |
| TUE 1/21 | 7:00 p.m. | Varsity | League | Normal | Away | BridgeportCentral | Loss | 71-79 | | Bridgeport Central High School-Barry McLeod Court | |
| FRI 1/24 | 7:00 p.m. | Varsity | League | Normal | Home | Stamford | Loss | 68-80 | | Darien High School-DHS Main Gym | |
| MON 1/27 | 7:00 p.m. | Varsity | League | Normal | Away | Ridgefield | Loss | 35-72 | | Ridgefield High School-Main Gym | |
| THU 1/30 | 7:00 p.m. | Varsity | League | Normal | Away | WarrenHarding | Win | 64-46 | | Warren Harding High School-Gym | |
| MON 2/3 | 7:00 p.m. | Varsity | League | Normal | Away | Westhill | Loss | 54-69 | | Westhill High School-Main Gym | |
| THU 2/6 | 7:00 p.m. | Varsity | League | Normal | Home | FairfieldLudlowe | Loss | 65-87 | | Darien High School-DHS Main Gym | |
| MON 2/10 | 7:00 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 42-74 | | Darien High School-DHS Main Gym | |
| THU 2/13 | 7:00 p.m. | Varsity | League | Normal | Away | Staples | Loss | 65-86 | | Staples High School-Staples Gym | |
| MON 2/17 | 7:00 p.m. | Varsity | League | Normal | Home | Norwalk | Loss | 61-69 | | Darien High School-DHS Main Gym | |
| WED 2/19 | 7:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 56-69 | | Fairfield Warde HS-Large Gym | |
| MON 2/24 | 7:00 p.m. | Varsity | League | Normal | Home | StJoseph | Loss | 94-104(OT) | | Darien High School-DHS Main Gym | |
| WED 2/26 | 7:00 p.m. | Varsity | League | Normal | Home | TrinityCatholic | Loss | 50-77 | | Darien High School-DHS Main Gym | |