| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 4/1 | 3:45 PM | Varsity | League | Normal | Away | Shepaug Valley | Win | 5-2 | | Shepaug Valley High School - Shepaug Valley Tennis Courts | |
| FRI 4/5 | 4:00 PM | Varsity | League | Normal | Home | East Granby | Win | 7-0 | | Thomaston High School - Nystrom Park | |
| MON 4/8 | 4:30 PM | Varsity | League | Normal | Home | Wamogo | Win | 6-1 | | Thomaston High School - Nystrom Park | |
| MON 4/22 | 3:45 PM | Varsity | League | Normal | Home | Nonnewaug | Loss | 1-6 | | Thomaston High School - Nystrom Park | |
| WED 4/24 | 3:45 PM | Varsity | League | Normal | Away | Litchfield | Loss | 0-7 | | Litchfield High School - LHS Tennis Courts | |
| THU 4/25 | 3:45 PM | Varsity | League | Normal | Home | Shepaug Valley | Win | 4-3 | | Thomaston High School - Nystrom Park | |
| MON 4/29 | 3:45 PM | Varsity | League | Normal | Home | Gilbert | Win | 7-0 | | Thomaston High School - Nystrom Park | |
| MON 4/29 | 5:50 PM | Varsity | League | Normal | Home | Gilbert | Win | 7-0 | | Thomaston High School - Nystrom Park | |
| TUE 4/30 | 3:45 PM | Varsity | League | Normal | Home | Northwestern | Win | 5-2 | | Thomaston High School - Nystrom Park | |
| WED 5/1 | 3:45 PM | Varsity | League | Normal | Away | Wamogo | Win | 7-0 | | Wamogo Regional High School - Tennis Courts | |
| FRI 5/3 | 3:45 PM | Varsity | League | Normal | Away | Northwestern | Win | 6-1 | | Northwestern Regional H.S. - Tennis Courts | |
| MON 5/6 | 3:45 PM | Varsity | League | Normal | Home | Housatonic Regional | Win | 5-2 | | Thomaston High School - Nystrom Park | |
| WED 5/8 | 3:45 PM | Varsity | League | Normal | Away | Nonnewaug | Loss | 0-7 | | Nonnewaug High School - Tennis Courts | |
| FRI 5/10 | 3:45 PM | Varsity | League | Normal | Home | Litchfield | Loss | 0-4 | | Thomaston High School - Nystrom Park | |
| MON 5/13 | 3:45 PM | Varsity | Non-League | Normal | Home | Windsor Locks | Win | 7-0 | | Thomaston High School - Nystrom Park | |
| THU 5/16 | 3:45 PM | Varsity | League | Normal | Away | Housatonic Regional | Win | 7-0 | | Town Field - Town Tennis Courts | 12:00 PM - 1 Bus |
| MON 5/20 | 8:15 AM | Varsity | Postseason | Normal | Away | Shepaug Valley | | | | Nonnewaug High School - Tennis Courts | |
| Gilbert | | |
| Nonnewaug | | |
| Housatonic Regional | | |
| Litchfield | | |
| Wamogo | | |
| Northwestern | | |
| WED 5/22 | 1:00 PM | Varsity | Postseason | Normal | Away | Shepaug Valley | | | | Nonnewaug High School - Tennis Courts | |
| Wamogo | | |
| Nonnewaug | | |
| Litchfield | | |
| | |
| Housatonic Regional | | |
| Northwestern | | |
| SAT 5/25 | 2:00 PM | Varsity | Postseason | Normal | Home | St. Paul Catholic | Loss | 3-4 | | Thomaston High School - Nystrom Park | |