| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 3/25 | 3:45 PM | Varsity | Scrimmage | Normal | Away | Joel Barlow | | | | Joel Barlow High School - Tennis Courts | 2:30 PM |
| FRI 3/29 | 10:00 AM | Varsity | Scrimmage | Normal | Home | Naugatuck | | | | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club | |
| MON 4/8 | 4:30 PM | Varsity | League | Normal | Away | Newtown | Win | 6-1 | | Newtown High School - NHS Tennis Courts | 3:30 PM |
| TUE 4/9 | 3:45 PM | Varsity | League | Normal | Away | Bethel | Win | 7-0 | | Bethel High School - BHS Tennis Courts | 2:30 PM |
| WED 4/10 | 4:15 PM | Varsity | League | Normal | Away | New Fairfield | Win | 7-0 | | New Fairfield High School - Tennis Courts | 3:00 PM |
| MON 4/15 | 10:00 AM | Varsity | League | Normal | Away | Joel Barlow | Win | 4-3 | | Joel Barlow High School - Tennis Courts | 8:30 AM |
| WED 4/17 | 10:00 AM | Varsity | League | Normal | Home | Bunnell | Win | 7-0 | | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club | |
| WED 4/24 | 3:45 PM | Varsity | League | Normal | Home | Weston | Loss | 3-4 | | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club | |
| MON 4/29 | 4:45 PM | Varsity | League | Normal | Home | Stratford | Win | 7-0 | | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club | |
| WED 5/1 | 3:45 PM | Varsity | League | Normal | Home | Notre Dame-Fairfield | Win | 7-0 | | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club | |
| FRI 5/3 | 3:45 PM | Varsity | League | Normal | Away | New Milford | Win | 7-0 | | New Milford High School - Tennis Courts - NMHS | 2:30 PM |
| MON 5/6 | 3:45 PM | Varsity | League | Normal | Home | Masuk | Win | 6-1 | | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club | |
| WED 5/8 | 3:45 PM | Varsity | League | Normal | Home | Immaculate | Win | 6-1 | | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club | |
| MON 5/13 | 3:45 PM | Varsity | League | Normal | Away | Brookfield | Loss | 3-4 | | Brookfield High School - BHS Tennis Courts | 2:30 PM |
| TUE 5/21 | 3:30 PM | Varsity | Non-League | Normal | Home | Litchfield | Loss | 3-4 | | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club | |
| FRI 5/24 | 4:00 PM | Varsity | Postseason | Normal | Home | Bethel | Win | 7-0 | | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club | |
| TUE 5/28 | 3:45 PM | Varsity | Postseason | Normal | Away | Guilford | Loss | 0-7 | | Guilford High School - GHS Tennis Courts | 2:00 PM |