| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 4/8 | 4:00 p.m. | Varsity | League | Normal | Away | Darien | Loss | 0-7 | | DHS Tennis Courts | |
| TUE 4/21 | 4:00 p.m. | Varsity | League | Normal | Away | Wilton | Loss | 0-7 | | Tennis Courts | |
| THU 4/23 | 4:00 p.m. | Varsity | League | Normal | Home | StJoseph | Loss | 0-7 | | Central H.S. Tennis Courts | |
| FRI 4/24 | 4:00 p.m. | Varsity | League | Normal | Home | BrienMcMahon | Loss | 0-7 | | Central H.S. Tennis Courts | |
| FRI 4/24 | 2:45 p.m. | Varsity | League | Normal | Home | Trumbull | Loss | 0-7 | | Central H.S. Tennis Courts | |
| MON 4/27 | 4:00 p.m. | Varsity | League | Normal | Away | Ridgefield | Loss | 0-7 | | RHS Tennis Courts | |
| TUE 4/28 | 4:00 p.m. | Varsity | League | Normal | Away | NewCanaan | Loss | 0-7 | | | |
| THU 4/30 | 4:00 p.m. | Varsity | League | Normal | Home | Danbury | Loss | 0-7 | | Central H.S. Tennis Courts | |
| MON 5/4 | 4:00 p.m. | Varsity | League | Normal | Home | Stamford | Loss | 0-7 | | Central H.S. Tennis Courts | |
| TUE 5/5 | 4:00 p.m. | Varsity | League | Normal | Home | Westhill | Loss | 0-6 | | Central H.S. Tennis Courts | |
| MON 5/11 | 4:00 p.m. | Varsity | League | Normal | Away | Staples | Loss | 0-7 | | Staples HS-Tennis Courts | |
| TUE 5/12 | 4:00 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 0-7 | | Central H.S. Tennis Courts | |
| WED 5/13 | 4:00 p.m. | Varsity | League | Normal | Away | TrinityCatholic | Loss | 0-7 | | Scalzi Park | |
| THU 5/14 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 0-7 | | FWHS Blake Courts | |
| MON 5/18 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Loss | 0-7 | | Fairfield Ludlowe Tennis Courts | |
| WED 5/20 | 4:00 p.m. | Varsity | League | Normal | Away | Norwalk | Loss | 0-7 | | Norwalk High School | |