| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 4/5 | 3:45 p.m. | Varsity | League | Normal | Home | NewMilford | Loss | 6-1 | | New Fairfield High School-Tennis Courts | |
| FRI 4/8 | 3:30 p.m. | Varsity | League | Normal | Away | Immaculate | Loss | 1-6 | | Immaculate High School-Rogers Park, Danbury | |
| MON 4/11 | 4:00 p.m. | Varsity | League | Normal | Home | Masuk | Loss | 6-1 | | New Fairfield High School-Tennis Courts | |
| TUE 4/12 | 4:00 p.m. | Varsity | League | Normal | Home | Brookfield | Loss | 6-1 | | New Fairfield High School-Tennis Courts | |
| WED 4/13 | 3:15 p.m. | Varsity | League | Normal | Away | Immaculate | Loss | 5-2 | | Immaculate High School-Rogers Park, Danbury | |
| WED 4/20 | 3:45 p.m. | Varsity | League | Normal | Away | Weston | Loss | 0-7 | | Weston High School-WHS Tennis Courts | |
| MON 4/25 | 3:45 p.m. | Varsity | League | Normal | Away | Pomperaug | Loss | 3-4 | | Pomperaug High School-Edgewood Bath & Tennis Club | |
| WED 4/27 | 3:30 p.m. | Varsity | League | Normal | Away | Newtown | Loss | 7-0 | | Newtown High School-NHS Tennis Courts | |
| FRI 4/29 | 4:00 p.m. | Varsity | League | Normal | Away | Bunnell | Win | 7-0 | | Bunnell HS | |
| TUE 5/3 | 5:00 p.m. | Varsity | League | Normal | Home | Bethel | Loss | 1-6 | | New Fairfield High School-Tennis Courts | |
| TUE 5/10 | 3:45 p.m. | Varsity | League | Normal | Away | Stratford | Win | 5-2 | | Flood Middle School-Flood MS Tennis Courts | |
| FRI 5/13 | 4:00 p.m. | Varsity | League | Normal | Home | JoelBarlow | Loss | 1-6 | | New Fairfield High School-Tennis Courts | |