| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 4/4 | 4:00 p.m. | Varsity | League | Normal | Home | Staples | Loss | 6-1 | | Brien McMahon HS | |
| THU 4/5 | 4:00 p.m. | Varsity | League | Normal | Home | Norwalk | Win | 6-1 | | Brien McMahon HS | |
| MON 4/9 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 0-7 | | FWHS Blake Courts | |
| TUE 4/10 | 4:00 p.m. | Varsity | League | Normal | Away | Greenwich | Loss | 7-0 | | GHS Tennis Courts | |
| THU 4/12 | 4:00 p.m. | Varsity | League | Normal | Home | Darien | Loss | 2-5 | | Brien McMahon HS | |
| TUE 4/24 | 4:00 p.m. | Varsity | League | Normal | Away | Danbury | Win | 4-3 | | Danbury High School Tennis Courts | |
| WED 4/25 | 4:00 p.m. | Varsity | League | Normal | Away | Westhill | Loss | 4-0 | | Westhill Tennis Courts | |
| THU 4/26 | 4:00 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 4-1 | | Brien McMahon HS | |
| MON 4/30 | 4:00 p.m. | Varsity | League | Normal | Home | TrinityCatholic | Win | 7-0 | | Brien McMahon HS | |
| THU 5/3 | 4:00 p.m. | Varsity | League | Normal | Home | Trumbull | Loss | 6-1 | | Brien McMahon HS | |
| MON 5/7 | 4:00 p.m. | Varsity | League | Normal | Away | Stamford | Win | 5-2 | | Stamford High School | |
| TUE 5/8 | 4:00 p.m. | Varsity | League | Normal | Away | BridgeportCentral | Win | 7-0 | | Central H.S. Tennis Courts | |
| WED 5/9 | 3:30 p.m. | Varsity | League | Normal | Away | Wilton | Loss | 7-0 | | Four Season Tennis Club | |
| THU 5/10 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Loss | 0-7 | | Fairfield Ludlowe Tennis Courts | |
| TUE 5/15 | 4:00 p.m. | Varsity | League | Normal | Home | StJoseph | Win | 4-1 | | Brien McMahon HS | |
| WED 5/16 | 5:00 p.m. | Varsity | League | Normal | Away | Ridgefield | Loss | 0-7 | | Ridgefield Tennis Club | |