| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 4/6 | 4:00 p.m. | Varsity | League | Normal | Away | Staples | Loss | 1-6 | | Staples HS-Tennis Courts | |
| FRI 4/8 | 4:00 p.m. | Varsity | League | Normal | Home | StJoseph | Win | 7-0 | | THS Tennis Courts | |
| WED 4/13 | 11:00 a.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 1-6 | | | |
| MON 4/18 | 4:00 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 1-6 | | THS Tennis Courts | |
| TUE 4/19 | 4:00 p.m. | Varsity | League | Normal | Away | Danbury | Win | 7-0 | | Danbury High School Tennis Courts | |
| THU 4/21 | 4:00 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 1-6 | | THS Tennis Courts | |
| MON 4/25 | 4:00 p.m. | Varsity | League | Normal | Away | Westhill | Win | 4-3 | | Westhill Tennis Courts | |
| WED 4/27 | 4:30 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Loss | 1-6 | | Fairfield Ludlowe Tennis Courts | |
| THU 5/5 | 4:00 p.m. | Varsity | League | Normal | Home | TrinityCatholic | Win | 7-0 | | THS Tennis Courts | |
| THU 5/5 | 6:30 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 3-4 | | Tashua Knolls Golf Course | |
| MON 5/9 | 6:00 p.m. | Varsity | League | Normal | Home | BrienMcMahon | Win | 5-2 | | Tashua Knolls Golf Course | |
| TUE 5/10 | 4:00 p.m. | Varsity | League | Normal | Away | Stamford | Win | 7-0 | | Stamford High School | |
| WED 5/11 | 4:00 p.m. | Varsity | League | Normal | Away | BridgeportCentral | Win | 7-0 | | | |
| THU 5/12 | 4:00 p.m. | Varsity | League | Normal | Home | Ridgefield | Win | 4-3 | | | |
| SAT 5/14 | 9:30 a.m. | Varsity | League | Normal | Home | Norwalk | Win | 7-0 | | THS Tennis Courts | |
| MON 5/16 | 4:00 p.m. | Varsity | League | Normal | Away | Darien | Loss | 0-7 | | DHS Tennis Courts | |