| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 4/1 | 3:45 PM | Varsity | League | Normal | Home | Fitch | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| FRI 4/5 | 3:45 PM | Varsity | League | Normal | Away | Killingly | Win | 7-0 | | Killingly High School - Tennis Courts | 2:00 PM - 1 Bus |
| FRI 4/12 | 2:30 PM | Varsity | League | Normal | Home | Newington | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| MON 4/15 | Canceled | Varsity | League | Canceled | Home | | | | | Stonington High School - SHS Tennis Courts | |
| TUE 4/16 | 3:45 PM | Varsity | League | Normal | Away | East Lyme | Win | 5-2 | | East Lyme High School - Tennis Courts | 2:00 PM - 1 Bus - w/ Baseball |
| WED 4/17 | 3:45 PM | Varsity | League | Normal | Home | Norwich Free Academy | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| FRI 4/19 | 4:00 PM | Varsity | League | Normal | Away | Lyman Memorial | Win | 7-0 | | Lyman Memorial High School - Tennis Courts | 2:30 PM - 1 Bus - w/ JV Baseball |
| TUE 4/23 | 4:00 PM | Varsity | League | Normal | Home | Daniel Hand | Win | 6-1 | | Stonington High School - SHS Tennis Courts | |
| THU 4/25 | 3:45 PM | Varsity | League | Normal | Home | Waterford | Win | 6-1 | | Stonington High School - SHS Tennis Courts | |
| FRI 4/26 | 3:45 PM | Varsity | League | Normal | Away | Fitch | Win | 7-0 | | Fitch High School - Main Tennis Courts | 2:30 PM - 1 Bus - w/ Gtennis |
| MON 4/29 | 3:45 PM | Varsity | League | Normal | Home | Ledyard | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| TUE 4/30 | 3:45 PM | Varsity | League | Normal | Home | Montville | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| WED 5/1 | 3:45 PM | Varsity | League | Normal | Home | St. Bernard - Wheeler | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| FRI 5/3 | 3:45 PM | Varsity | League | Normal | Home | East Lyme | Win | 5-2 | | Stonington High School - SHS Tennis Courts | |
| MON 5/6 | 4:15 PM | Varsity | League | Normal | Home | Woodstock Academy | Win | 7-0 | | Stonington High School - SHS Tennis Courts | |
| WED 5/8 | 3:45 PM | Varsity | League | Normal | Away | Waterford | Win | 5-2 | | Waterford High School - Tennis Courts - WHS | 2:20 PM - 1 Bus |
| MON 5/20 | 3:00 PM | Varsity | Postseason | Normal | Away | | Tied | | | East Lyme High School - Tennis Courts | |
| East Lyme | Tied | |
| Fitch | Tied | |
| Killingly | Tied | |
| Ledyard | Tied | |
| Lyman Memorial | Tied | |
| Montville | Tied | |
| Norwich Free Academy | Tied | |
| St. Bernard - Wheeler | Tied | |
| Waterford | Tied | |
| Woodstock Academy | Tied | |
| TUE 5/21 | 3:00 PM | Varsity | Postseason | Normal | Away | | | | | East Lyme High School - Tennis Courts | |
| | |
| East Lyme | | |
| Fitch | | |
| Ledyard | | |
| Lyman Memorial | | |
| Montville | | |
| Norwich Free Academy | | |
| St. Bernard - Wheeler | | |
| Waterford | | |
| Woodstock Academy | | |
| WED 5/22 | 3:00 PM | Varsity | Postseason | Normal | Home | | | | | Stonington High School - SHS Tennis Courts | |
| | |
| East Lyme | | |
| Fitch | | |
| Ledyard | | |
| Lyman Memorial | | |
| Montville | | |
| Norwich Free Academy | | |
| St. Bernard - Wheeler | | |
| Waterford | | |
| Woodstock Academy | | |