| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 4/3 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 0-7 | | FWHS Knapps Courts | |
| WED 4/5 | 4:00 p.m. | Varsity | League | Normal | Away | Wilton | Loss | 0-7 | | Wilton Tennis Courts | |
| FRI 4/7 | 4:00 p.m. | Varsity | League | Normal | Away | StJoseph | Loss | 1-6 | | St. Joseph High School | |
| TUE 4/11 | 10:00 a.m. | Varsity | League | Normal | Away | Staples | Loss | 0-7 | | Staples HS-Tennis Courts | |
| WED 4/12 | 1:30 p.m. | Varsity | League | Normal | Away | Westhill | Loss | 0-7 | | shippan raquet club | |
| MON 4/17 | 4:00 p.m. | Varsity | League | Normal | Away | TrinityCatholic | Loss | 3-4 | | Scalzi Park | |
| THU 4/20 | 4:00 p.m. | Varsity | League | Normal | Away | BridgeportCentral | Win | 6-1 | | Bridgeport Central | |
| THU 4/27 | 5:15 p.m. | Varsity | League | Normal | Away | NewCanaan | Loss | 0-7 | | NCHS Tennis Courts | |
| FRI 4/28 | 5:00 p.m. | Varsity | League | Normal | Away | Greenwich | Loss | 0-7 | | GHS Tennis Courts | |
| MON 5/1 | 5:30 p.m. | Varsity | League | Normal | Home | Danbury | Loss | 1-6 | | Brien McMahon High School | |
| TUE 5/2 | 5:00 p.m. | Varsity | League | Normal | Home | BrienMcMahon | Loss | 1-6 | | Brien McMahon High School | |
| THU 5/4 | 4:00 p.m. | Varsity | League | Normal | Away | Stamford | Loss | 0-7 | | | |
| MON 5/8 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Loss | 0-7 | | Fairfield Ludlowe Tennis Courts | |
| TUE 5/9 | 4:30 p.m. | Varsity | League | Normal | Away | Ridgefield | Loss | 0-7 | | RHS Tennis Courts | |
| THU 5/11 | 4:00 p.m. | Varsity | League | Normal | Away | Trumbull | Loss | 0-7 | | Unity Park | |
| FRI 5/12 | 4:15 p.m. | Varsity | League | Normal | Home | HenryAbbottRVT | Win | 7-0 | | Brien McMahon High School | |
| MON 5/15 | 4:00 p.m. | Varsity | League | Normal | Away | Darien | Loss | 0-7 | | DHS Tennis Courts | |