| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 3/25 | 4:30 PM | Varsity | Scrimmage | Normal | Away | | | | | The Frederick Gunn School - Tennis Courts | 4:00 PM |
| MON 4/1 | 3:45 PM | Varsity | League | Normal | Away | Thomaston | Win | 5-0 | | Thomaston High School - Nystrom Park | 2:00 PM |
| MON 4/8 | 3:45 PM | Varsity | League | Normal | Away | Northwestern | Win | 5-0 | | Northwestern Regional H.S. - Tennis Courts | 2:00 PM |
| TUE 4/9 | 3:45 PM | Varsity | League | Normal | Away | Housatonic Regional | Win | 4-1 | | Town Field - Town Tennis Courts | 2:00 PM |
| WED 4/10 | 3:45 PM | Varsity | League | Normal | Away | Wamogo | Win | 5-0 | | Wamogo Regional High School - Tennis Courts | 2:25 PM |
| MON 4/22 | 3:45 PM | Varsity | Non-League | Normal | Home | Abbott Tech | Win | 6-1 | | Shepaug Valley High School - Shepaug Valley Tennis Courts | |
| TUE 4/23 | 3:45 PM | Varsity | League | Normal | Home | Litchfield | Win | 5-0 | | Shepaug Valley High School - Shepaug Valley Tennis Courts | |
| WED 4/24 | 3:45 PM | Varsity | League | Normal | Away | Nonnewaug | Win | 4-1 | | Nonnewaug High School - Tennis Courts | 2:25 PM |
| THU 4/25 | 3:45 PM | Varsity | League | Normal | Home | Thomaston | Win | 5-0 | | Shepaug Valley High School - Shepaug Valley Tennis Courts | |
| MON 4/29 | 3:45 PM | Varsity | League | Normal | Home | Housatonic Regional | Win | 5-0 | | Shepaug Valley High School - Shepaug Valley Tennis Courts | |
| WED 5/1 | 3:45 PM | Varsity | League | Normal | Home | Northwestern | Win | 5-0 | | Shepaug Valley High School - Shepaug Valley Tennis Courts | |
| FRI 5/3 | 3:45 PM | Varsity | League | Normal | Away | Litchfield | Win | 4-1 | | Litchfield High School - LHS Tennis Courts | 2:25 PM |
| MON 5/6 | 3:45 PM | Varsity | League | Normal | Home | Wamogo | Win | 5-0 | | Shepaug Valley High School - Shepaug Valley Tennis Courts | |
| WED 5/8 | 4:00 PM | Varsity | League | Normal | Away | Granby Memorial | Win | 6-1 | | Granby Memorial High School - Tennis Courts | 2:00 PM |
| FRI 5/10 | 3:45 PM | Varsity | League | Normal | Home | Nonnewaug | Loss | 2-3 | | Shepaug Valley High School - Shepaug Valley Tennis Courts | |
| TUE 5/14 | 2:00 PM | Varsity | Postseason | Normal | Away | Gilbert | | | | Nonnewaug High School - Tennis Courts | 12:30 PM |
| Housatonic Regional | | |
| Litchfield | | |
| Nonnewaug | | |
| Northwestern | | |
| Thomaston | | |
| Wamogo | | |
| MON 5/20 | 12:01 AM | Varsity | Postseason | Normal | Away | Gilbert | | | | TBA - TBA | 11:30 AM |
| Housatonic Regional | | |
| Litchfield | | |
| Nonnewaug | | |
| Northwestern | | |
| Thomaston | | |
| Wamogo | | |
| WED 5/22 | 4:00 PM | Varsity | Postseason | Normal | Away | Housatonic Regional | | | | Thomaston Nystrom Park - Nystroms Park courts | |
| Litchfield | | |
| Nonnewaug | | |
| FRI 5/24 | 1:00 PM | Varsity | Postseason | Normal | Home | Housatonic Regional | Win | 6-1 | | Shepaug Valley High School - Shepaug Valley Tennis Courts | |
| TUE 5/28 | 1:00 PM | Varsity | Postseason | Normal | Home | Nonnewaug | Loss | 1-6 | | Shepaug Valley High School - Shepaug Valley Tennis Courts | |