| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 3/28 | Canceled | Varsity | Scrimmage | Canceled | Home | Rocky Hill | | | | Stonington High School - SHS Tennis Courts | |
| FRI 3/29 | 10:00 AM | Varsity | Scrimmage | Normal | Away | Rocky Hill | | | | Rocky Hill High School - tennis courts | 8:30 AM - 1 Bus |
| FRI 4/5 | 3:45 PM | Varsity | League | Normal | Home | Norwich Free Academy | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| TUE 4/16 | 4:00 PM | Varsity | League | Normal | Home | Killingly | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| WED 4/17 | 3:45 PM | Varsity | League | Normal | Away | East Lyme | Win | 7-0 | | East Lyme High School - Tennis Courts | 1:45 PM - 1 Bus - w/ Golf |
| FRI 4/19 | 3:45 PM | Varsity | League | Normal | Away | Fitch | Win | 5-2 | | Fitch High School - Main Tennis Courts | 2:20 PM - 1 Bus |
| WED 4/24 | 4:00 PM | Varsity | League | Normal | Home | Lyman Memorial | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| FRI 4/26 | 3:45 PM | Varsity | League | Normal | Away | Waterford | Win | 5-2 | | Waterford High School - Tennis Courts - WHS | 2:30 PM - 1 Bus - w/ Btennis |
| TUE 4/30 | 3:45 PM | Varsity | League | Normal | Home | Montville | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| THU 5/2 | 3:45 PM | Varsity | League | Normal | Home | Fitch | Win | 6-1 | | Stonington High School - SHS Tennis Courts | |
| SAT 5/4 | 11:00 AM | Varsity | League | Normal | Home | Windham / Windham Tech | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| TUE 5/7 | 3:45 PM | Varsity | League | Normal | Away | Ledyard | Win | 6-1 | | Ledyard High School - Tennis Courts | 2:20 PM - 1 Bus |
| WED 5/8 | 3:45 PM | Varsity | Non-League | Normal | Away | Old Lyme | Win | 4-3 | | Lyme-Old Lyme High School - Tennis Courts | 2:00 PM - 1 Bus |
| FRI 5/10 | 3:45 PM | Varsity | League | Normal | Home | East Lyme | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| MON 5/13 | 4:15 PM | Varsity | League | Normal | Home | Woodstock Academy | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| TUE 5/14 | 3:15 PM | Varsity | League | Normal | Home | Waterford | Win | 6-1 | | Stonington High School - SHS Tennis Courts | |
| SUN 5/19 | 1:00 PM | Varsity | Non-League | Normal | Away | Daniel Hand | Win | 6-1 | | Polson Middle School, Madison - Polson Tennis Courts/DHHS Campus | 11:00 AM - 1 Bus |
| MON 5/20 | 3:00 PM | Varsity | Postseason | Normal | Home | | | | | Stonington High School - SHS Tennis Courts | |
| East Lyme | | |
| Fitch | | |
| Killingly | | |
| Ledyard | | |
| Lyman Memorial | | |
| Montville | | |
| Norwich Free Academy | | |
| St. Bernard | | |
| Waterford | | |
| Windham / Windham Tech | | |
| Woodstock Academy | | |
| TUE 5/21 | 3:00 PM | Varsity | Postseason | Normal | Home | | | | | Stonington High School - SHS Tennis Courts | |
| East Lyme | | |
| Fitch | | |
| Killingly | | |
| Ledyard | | |
| Lyman Memorial | | |
| Montville | | |
| Norwich Free Academy | | |
| St. Bernard | | |
| Waterford | | |
| Windham / Windham Tech | | |
| Woodstock Academy | | |
| WED 5/22 | 3:00 PM | Varsity | Postseason | Normal | Home | | | | | Stonington High School - SHS Tennis Courts | |
| East Lyme | | |
| Fitch | | |
| Killingly | | |
| Ledyard | | |
| Lyman Memorial | | |
| Montville | | |
| Norwich Free Academy | | |
| St. Bernard | | |
| Waterford | | |
| Windham / Windham Tech | | |
| Woodstock Academy | | |