| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 4/5 | 4:00 p.m. | Varsity | League | Normal | Away | Stamford | Win | 5-2 | | Stamford High School | |
| SAT 4/7 | 3:00 p.m. | Varsity | League | Normal | Home | Ridgefield | Loss | 3-4 | | THS Tennis Courts | |
| TUE 4/17 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Loss | 2-5 | | Fairfield Ludlowe Tennis Courts | |
| WED 4/18 | 4:00 p.m. | Varsity | League | Normal | Away | Darien | Loss | 0-7 | | DHS Tennis Courts | |
| FRI 4/20 | 4:00 p.m. | Varsity | League | Normal | Away | Staples | Loss | 0-7 | | Staples HS-Tennis Courts | |
| TUE 4/24 | 4:00 p.m. | Varsity | League | Normal | Away | Westhill | Loss | 1-6 | | Cummings Park Tennis Courts | |
| THU 4/26 | 4:30 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 0-7 | | THS Tennis Courts | |
| SAT 4/28 | 12:00 p.m. | Varsity | League | Normal | Home | BrienMcMahon | Win | 5-2 | | THS Tennis Courts | |
| MON 4/30 | 4:00 p.m. | Varsity | League | Normal | Home | StJoseph | Win | 4-3 | | THS Tennis Courts | |
| TUE 5/1 | 4:00 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 0-7 | | THS Tennis Courts | |
| THU 5/3 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Win | 4-0 | | Fairfield Woods Middle School Courts | |
| SAT 5/5 | 12:00 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 1-6 | | THS Tennis Courts | |
| MON 5/7 | 4:00 p.m. | Varsity | League | Normal | Home | Norwalk | Win | 7-0 | | THS Tennis Courts | |
| TUE 5/8 | 4:00 p.m. | Varsity | League | Normal | Home | TrinityCatholic | Win | 7-0 | | THS Tennis Courts | |
| THU 5/10 | 4:00 p.m. | Varsity | League | Normal | Away | BridgeportCentral | Win | 7-0 | | Central H.S. Tennis Courts | |
| MON 5/14 | 4:00 p.m. | Varsity | League | Normal | Away | Danbury | Win | 7-0 | | Danbury High School Tennis Courts | |