| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 4/1 | 4:00 PM | Varsity | League | Normal | Away | Old Lyme | Loss | 0-7 | | Lyme-Old Lyme High School - Tennis Courts | 2:30 PM |
| FRI 4/5 | 4:00 PM | Varsity | League | Normal | Home | Portland | Loss | 3-4 | | East Hampton High School - Tennis Courts | |
| TUE 4/16 | 3:45 PM | Varsity | League | Normal | Away | Valley Regional | Loss | 1-6 | | Valley Regional High School - Tennis Courts | |
| WED 4/17 | 4:00 PM | Varsity | League | Normal | Away | Cromwell | Loss | 2-3 | | Watrous park - Watrous park | |
| TUE 4/23 | Postponed | Varsity | League | Postponed | Away | Coginchaug | | | | Coginchaug Regional High School - Tennis Courts @ CRHS | |
| THU 4/25 | 3:45 PM | Varsity | League | Normal | Away | Morgan | Loss | 0-7 | | Morgan School - Tennis Courts | 2:30 PM |
| WED 5/1 | 4:00 PM | Varsity | League | Normal | Away | Coginchaug | Loss | 1-6 | | Coginchaug Regional High School - Tennis Courts @ CRHS | 2:30 PM |
| THU 5/2 | 3:45 PM | Varsity | League | Normal | Away | Westbrook | Loss | 1-6 | | Westbrook High School - Westbrook HS / MS Tennis Courts | 2:30 PM |
| FRI 5/3 | 3:45 PM | Varsity | League | Normal | Away | Haddam Killingworth | Win | 5-2 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| TUE 5/7 | 3:45 PM | Varsity | League | Normal | Away | Haddam Killingworth | Loss | 3-4 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | 2:30 PM |
| WED 5/8 | 4:00 PM | Varsity | League | Normal | Away | Cromwell | Win | 5-2 | | Watrous park - Watrous park | 2:30 PM |
| THU 5/9 | 4:00 PM | Varsity | League | Normal | Away | Old Saybrook | Loss | 2-5 | | Old Saybrook High School - Old Saybrook Tennis Courts | |
| SAT 5/11 | 12:00 AM | Varsity | League | Normal | Away | Old Lyme | Loss | 1-6 | | Lyme-Old Lyme High School - Tennis Courts | |
| MON 5/13 | 4:00 PM | Varsity | Non-League | Normal | Away | Westbrook | Loss | 1-6 | | Westbrook High School - Westbrook HS / MS Tennis Courts | |
| TUE 5/14 | 3:45 PM | Varsity | Non-League | Normal | Away | Portland | Loss | 0-7 | | Portland High School - Tennis Courts | |
| FRI 5/17 | 2:30 PM | Varsity | League | Normal | Away | North Branford | Loss | 3-4 | | North Branford High School - NBHS Tennis Courts | 2:30 PM |
| MON 5/20 | 9:00 AM | Varsity | Postseason | Normal | Away | North Branford | | | | Not Listed | |
| Coginchaug | | |
| Cromwell | | |
| Haddam Killingworth | | |
| Morgan | | |
| | |
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| Portland | | |
| Westbrook | | |
| Old Lyme | | |
| Old Saybrook | | |
| Valley Regional | | |
| TUE 5/21 | 12:00 PM | Varsity | Postseason | Normal | Away | Valley Regional | | | | Lyme-Old Lyme High School - Tennis Courts | |
| Old Saybrook | | |
| Old Lyme | | |
| Westbrook | | |
| Portland | | |
| | |
| | |
| Morgan | | |
| Haddam Killingworth | | |
| Cromwell | | |
| Coginchaug | | |
| North Branford | | |