| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 4/5 | 5:30 p.m. | Varsity | League | Normal | Home | Immaculate | Win | 6-1 | | Edgewood Bath and Tennis Club | |
| TUE 4/11 | 10:00 a.m. | Varsity | League | Normal | Away | Brookfield | Loss | 6-1 | | Brookfield High School-BHS Tennis Courts | |
| WED 4/12 | 10:00 a.m. | Varsity | League | Normal | Home | Weston | Loss | 7-0 | | Edgewood Bath and Tennis Club | |
| TUE 4/18 | 3:45 p.m. | Varsity | League | Normal | Away | Bethel | Loss | 4-3 | | Bethel High School-BHS Tennis Courts | |
| WED 4/19 | 3:45 p.m. | Varsity | League | Normal | Away | Newtown | Loss | 6-1 | | Newtown High School-NHS Tennis Courts | |
| MON 4/24 | 3:45 p.m. | Varsity | League | Normal | Away | NewFairfield | Win | 7-0 | | New Fairfield High School-Tennis Courts | |
| WED 4/26 | 3:45 p.m. | Varsity | League | Normal | Away | JoelBarlow | Loss | 5-2 | | Joel Barlow High School-Tennis Courts | |
| FRI 4/28 | 4:00 p.m. | Varsity | League | Normal | Home | HCWilcoxRVT | Win | 7-0 | | Edgewood Bath and Tennis Club | |
| MON 5/1 | 4:00 p.m. | Varsity | League | Normal | Home | Bunnell | Win | 7-0 | | Edgewood Bath and Tennis Club | |
| THU 5/4 | 3:00 p.m. | Varsity | League | Normal | Away | Nonnewaug | Loss | 3-4 | | Nonnewaug High School-Tennis Courts | |
| FRI 5/5 | 4:00 p.m. | Varsity | League | Normal | Home | Stratford | Win | 6-1 | | Edgewood Bath and Tennis Club | |
| MON 5/8 | 3:30 p.m. | Varsity | League | Normal | Away | Naugatuck | Win | 6-1 | | Naugatuck High School-Tennis Courts | |
| WED 5/10 | 3:45 p.m. | Varsity | League | Normal | Away | NewMilford | Loss | 5-2 | | New Milford High School-Tennis Courts - NMHS | |
| MON 5/15 | 4:00 p.m. | Varsity | League | Normal | Home | Masuk | Loss | 4-3 | | Edgewood Bath and Tennis Club | |
| TUE 5/23 | 4:00 p.m. | Varsity | League | Normal | Away | HCWilcoxRVT | Win | 7-0 | | Wilcox Tech-Tennis Courts | |