| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 4/1 | 4:00 PM | Varsity | League | Normal | Home | Waterford | Loss | 0-7 | | Lyman Memorial High School - Tennis Courts | |
| FRI 4/5 | 4:00 PM | Varsity | League | Normal | Home | Fitch | Loss | 0-7 | | Lyman Memorial High School - Tennis Courts | |
| MON 4/15 | 3:45 PM | Varsity | League | Normal | Home | St. Bernard | Loss | 1-6 | | Lyman Memorial High School - Tennis Courts | |
| WED 4/24 | 4:00 PM | Varsity | League | Normal | Away | Stonington | Loss | 0-7 | | Stonington High School - SHS Tennis Courts | 2:00 PM |
| MON 4/29 | 3:45 PM | Varsity | League | Normal | Home | Windham / Windham Tech | Loss | 2-5 | | Lyman Memorial High School - Tennis Courts | |
| THU 5/2 | 3:45 PM | Varsity | League | Normal | Home | Windham / Windham Tech | Loss | 2-5 | | Lyman Memorial High School - Tennis Courts | |
| FRI 5/3 | 4:00 PM | Varsity | League | Normal | Home | Ledyard | Loss | 1-6 | | Lyman Memorial High School - Tennis Courts | |
| MON 5/6 | 4:00 PM | Varsity | League | Normal | Home | Montville | Loss | 3-4 | | Lyman Memorial High School - Tennis Courts | |
| MON 5/6 | 2:00 PM | Varsity | League | Normal | Home | Montville | Win | 6-1 | | Lyman Memorial High School - Tennis Courts | |
| TUE 5/7 | 6:15 PM | Varsity | League | Normal | Away | Woodstock Academy | Loss | 0-7 | | Pomfret School - Outside Tennis Courts | 4:30 PM |
| WED 5/8 | 2:45 PM | Varsity | League | Normal | Away | New London | Win | 5-2 | | New London High School - NLHS Tennis Courts | 1:15 PM |
| THU 5/9 | 3:45 PM | Varsity | League | Normal | Away | St. Bernard | Loss | 2-5 | | St. Bernard School - Tennis Courts | 2:20 PM |
| WED 5/15 | Postponed | Varsity | League | Postponed | Home | New London | | | | Lyman Memorial High School - Tennis Courts | |
| MON 5/20 | 3:00 PM | Varsity | Postseason | Normal | Away | East Lyme | | | | Stonington High School - SHS Tennis Courts | |
| Woodstock Academy | | |
| Waterford | | |
| Norwich Free Academy | | |
| Montville | | |
| Stonington | | |
| Fitch | | |
| Windham / Windham Tech | | |
| Killingly | | |
| Ledyard | | |
| | |
| St. Bernard | | |
| TUE 5/21 | 3:00 PM | Varsity | Postseason | Normal | Away | Woodstock Academy | | | | Stonington High School - SHS Tennis Courts | |
| East Lyme | | |
| Norwich Free Academy | | |
| Waterford | | |
| Windham / Windham Tech | | |
| Montville | | |
| Stonington | | |
| Fitch | | |
| | |
| | |
| Ledyard | | |
| St. Bernard | | |
| WED 5/22 | 3:00 PM | Varsity | Postseason | Normal | Away | Woodstock Academy | | | | Stonington High School - SHS Tennis Courts | |
| East Lyme | | |
| Norwich Free Academy | | |
| Waterford | | |
| Windham / Windham Tech | | |
| Montville | | |
| Stonington | | |
| Ledyard | | |
| | |
| | |
| Fitch | | |
| St. Bernard | | |