| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 3/26 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Guilford | | | | Guilford High School - GHS Tennis Courts | 2:40 PM |
| MON 4/1 | 4:00 PM | Varsity | League | Normal | Away | East Hampton/Portland | Win | 5-2 | | East Hampton High School - Tennis Courts | 2:30 PM |
| FRI 4/5 | 4:00 PM | Varsity | League | Normal | Away | Old Saybrook | Win | 5-2 | | Old Saybrook High School - Old Saybrook Tennis Courts | 2:50 PM |
| WED 4/10 | 2:00 PM | Varsity | League | Normal | Home | Coginchaug | Win | 5-2 | | Lyme-Old Lyme High School - Tennis Courts | |
| WED 4/17 | 4:00 PM | Varsity | League | Normal | Home | Morgan | Win | 5-2 | | Lyme-Old Lyme High School - Tennis Courts | |
| FRI 4/19 | 3:45 PM | Varsity | League | Normal | Away | Haddam Killingworth | Win | 4-3 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | 2:15 PM |
| MON 4/22 | 4:00 PM | Varsity | League | Normal | Home | Valley Regional | Loss | 3-4 | | Lyme-Old Lyme High School - Tennis Courts | |
| WED 4/24 | 4:00 PM | Varsity | League | Normal | Home | Cromwell | Win | 5-2 | | Lyme-Old Lyme High School - Tennis Courts | |
| FRI 4/26 | 3:15 PM | Varsity | League | Normal | Away | Westbrook | Loss | 0-7 | | Westbrook High School - Westbrook HS / MS Tennis Courts | 2:45 PM |
| MON 4/29 | 5:00 PM | Varsity | League | Normal | Home | East Hampton/Portland | Win | 5-2 | | Lyme-Old Lyme High School - Tennis Courts | |
| WED 5/1 | 3:45 PM | Varsity | League | Normal | Away | Valley Regional | Loss | 2-5 | | Valley Regional High School - Tennis Courts | 2:30 PM |
| FRI 5/3 | 4:00 PM | Varsity | League | Normal | Away | Coginchaug | Win | 6-1 | | Coginchaug Regional High School - Tennis Courts @ CRHS | 2:15 PM |
| MON 5/6 | 4:00 PM | Varsity | League | Normal | Home | Old Saybrook | Win | 6-1 | | Lyme-Old Lyme High School - Tennis Courts | |
| THU 5/9 | 3:45 PM | Varsity | Non-League | Normal | Home | Haddam Killingworth | Win | 5-2 | | Lyme-Old Lyme High School - Tennis Courts | |
| FRI 5/10 | 3:45 PM | Varsity | Non-League | Normal | Home | Fitch | Loss | 1-6 | | Lyme-Old Lyme High School - Tennis Courts | |
| TUE 5/14 | 3:45 PM | Varsity | Non-League | Normal | Away | Ledyard | Win | 4-3 | | Ledyard High School - Tennis Courts | 2:15 PM |
| SAT 5/18 | Canceled | Varsity | Non-League | Canceled | Away | Waterford | | | | Waterford High School - Tennis Courts - WHS | 10:45 AM |
| MON 5/20 | 9:00 AM | Varsity | Postseason | Normal | Away | | | | | Not Listed | 7:40 AM |
| Coginchaug | | |
| Cromwell | | |
| East Hampton/Portland | | |
| Haddam Killingworth | | |
| Morgan | | |
| North Branford | | |
| Old Saybrook | | |
| Valley Regional | | |
| Westbrook | | |
| TUE 5/21 | 4:00 PM | Varsity | Postseason | Normal | Away | | | | | Morgan School - Tennis Courts | 2:45 PM |
| Coginchaug | | |
| Cromwell | | |
| East Hampton/Portland | | |
| Haddam Killingworth | | |
| Morgan | | |
| | |
| North Branford | | |
| Old Saybrook | | |
| Valley Regional | | |
| WED 5/22 | 6:00 PM | Varsity | Non-League | Normal | Away | Morgan | Win | 4-3 | | Morgan School - Tennis Courts | 4:45 PM |
| SAT 5/25 | 2:00 PM | Varsity | Postseason | Normal | Home | Valley Regional | Win | 6-1 | | Lyme-Old Lyme High School - Tennis Courts | |
| TUE 5/28 | 2:00 PM | Varsity | Postseason | Normal | Away | Westbrook | Loss | 3-4 | | Westbrook High School - Westbrook HS / MS Tennis Courts | 12:45 PM |