| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 3/27 | 3:45 PM | Varsity | Scrimmage | Normal | Away | Daniel Hand | | | | Westbrook High School - Westbrook HS / MS Tennis Courts | 2:30 PM |
| Westbrook | | |
| MON 4/1 | 4:00 PM | Varsity | League | Normal | Away | Lyman Memorial | Win | 7-0 | | Lyman Memorial High School - Tennis Courts | 2:30 PM |
| FRI 4/5 | 3:45 PM | Varsity | League | Normal | Home | St. Bernard | Win | 6-1 | | Waterford High School - Tennis Courts - WHS | |
| MON 4/15 | 3:45 PM | Varsity | League | Normal | Away | East Lyme | Win | 5-2 | | East Lyme High School - Tennis Courts | 2:30 PM |
| FRI 4/19 | 3:45 PM | Varsity | Non-League | Normal | Home | Guilford | Loss | 1-6 | | Waterford High School - Tennis Courts - WHS | |
| WED 4/24 | 3:45 PM | Varsity | League | Normal | Home | Windham / Windham Tech | Win | 7-0 | | Waterford High School - Tennis Courts - WHS | |
| FRI 4/26 | 3:45 PM | Varsity | League | Normal | Home | Stonington | Loss | 2-5 | | Waterford High School - Tennis Courts - WHS | |
| WED 5/1 | 5:30 PM | Varsity | League | Normal | Home | East Lyme | Win | 5-2 | | Waterford High School - Tennis Courts - WHS | |
| THU 5/2 | 3:45 PM | Varsity | League | Normal | Away | Killingly | Win | 7-0 | | Killingly High School - Tennis Courts | 2:30 PM |
| SAT 5/4 | 9:00 AM | Varsity | Non-League | Normal | Away | Old Lyme | Win | 4-3 | | Lyme-Old Lyme High School - Tennis Courts | 8:00 AM |
| MON 5/6 | 6:45 PM | Varsity | League | Normal | Away | Woodstock Academy | Win | 7-0 | | Pomfret School - Field House | 5:00 PM |
| TUE 5/7 | 5:00 PM | Varsity | League | Normal | Home | Montville | Win | 7-0 | | Waterford High School - Tennis Courts - WHS | |
| FRI 5/10 | 3:45 PM | Varsity | League | Normal | Away | Fitch | Win | 4-3 | | Fitch High School - Main Tennis Courts | 2:30 PM |
| MON 5/13 | 3:45 PM | Varsity | League | Normal | Home | Ledyard | Win | 5-2 | | Waterford High School - Tennis Courts - WHS | |
| TUE 5/14 | 3:15 PM | Varsity | League | Normal | Away | Stonington | Loss | 1-6 | | Stonington High School - SHS Tennis Courts | 1:30 PM |
| FRI 5/17 | 5:00 PM | Varsity | League | Normal | Home | Fitch | Win | 5-2 | | Waterford High School - Tennis Courts - WHS | |
| MON 5/20 | 3:00 PM | Varsity | Postseason | Normal | Away | | | | | Stonington High School - SHS Tennis Courts | |
| East Lyme | | |
| Fitch | | |
| Killingly | | |
| Ledyard | | |
| Lyman Memorial | | |
| Montville | | |
| Norwich Free Academy | | |
| St. Bernard | | |
| Stonington | | |
| Windham / Windham Tech | | |
| Woodstock Academy | | |
| TUE 5/21 | 3:00 PM | Varsity | Postseason | Normal | Away | | | | | Stonington High School - SHS Tennis Courts | |
| East Lyme | | |
| Fitch | | |
| Killingly | | |
| Ledyard | | |
| Lyman Memorial | | |
| Montville | | |
| Norwich Free Academy | | |
| St. Bernard | | |
| Stonington | | |
| Windham / Windham Tech | | |
| Woodstock Academy | | |
| WED 5/22 | 3:00 PM | Varsity | Postseason | Normal | Away | | | | | Stonington High School - SHS Tennis Courts | |
| East Lyme | | |
| Fitch | | |
| Killingly | | |
| Ledyard | | |
| Lyman Memorial | | |
| Montville | | |
| Norwich Free Academy | | |
| St. Bernard | | |
| Stonington | | |
| Windham / Windham Tech | | |
| Woodstock Academy | | |