| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 4/5 | 4:00 p.m. | Varsity | League | Normal | Home | Ridgefield | Loss | 0-7 | | Central H.S. Tennis Courts | |
| MON 4/9 | 4:00 p.m. | Varsity | League | Normal | Away | StJoseph | Loss | 0-7 | | | |
| TUE 4/10 | 4:00 p.m. | Varsity | League | Normal | Home | Staples | Loss | 0-7 | | Central H.S. Tennis Courts | |
| MON 4/16 | 11:00 a.m. | Varsity | League | Normal | Away | Norwalk | Loss | 2-5 | | Norwalk High School | |
| MON 4/23 | 4:00 p.m. | Varsity | League | Normal | Home | FairfieldWarde | Loss | 0-7 | | Central H.S. Tennis Courts | |
| TUE 4/24 | 4:00 p.m. | Varsity | League | Normal | Away | Westhill | Loss | 0-7 | | Westhill Tennis Courts | |
| MON 4/30 | 4:00 p.m. | Varsity | League | Normal | Home | FairfieldLudlowe | Loss | 0-7 | | Central H.S. Tennis Courts | |
| THU 5/3 | 4:00 p.m. | Varsity | League | Normal | Home | Darien | Loss | 0-7 | | Central H.S. Tennis Courts | |
| FRI 5/4 | 4:00 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 0-7 | | Central H.S. Tennis Courts | |
| MON 5/7 | 4:00 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 0-7 | | Central H.S. Tennis Courts | |
| TUE 5/8 | 4:00 p.m. | Varsity | League | Normal | Away | BrienMcMahon | Loss | 5-0 | | | |
| THU 5/10 | 4:00 p.m. | Varsity | League | Normal | Home | TrinityCatholic | Win | 4-3 | | Central H.S. Tennis Courts | |
| MON 5/14 | 4:00 p.m. | Varsity | League | Normal | Away | Trumbull | Loss | 0-7 | | Trumbull H.S. | |
| WED 5/16 | 3:00 p.m. | Varsity | League | Normal | Away | Greenwich | Loss | 0-7 | | GHS Tennis Courts | |
| THU 5/17 | 4:00 p.m. | Varsity | League | Normal | Away | Danbury | Loss | 0-7 | | Danbury High School Tennis Courts | |
| WED 5/23 | 4:00 p.m. | Varsity | League | Normal | Away | Stamford | Loss | 0-7 | | Stamford High School | |