| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 4/1 | 3:45 PM | Varsity | League | Normal | Away | Westbrook | Loss | 0-7 | | Westbrook High School - Westbrook HS / MS Tennis Courts | |
| MON 4/15 | 3:45 PM | Varsity | League | Normal | Home | North Branford | Win | 4-3 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| WED 4/17 | 4:00 PM | Varsity | League | Normal | Home | Old Saybrook | Loss | 2-5 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| FRI 4/19 | 4:00 PM | Varsity | League | Normal | Away | Old Lyme | Loss | 0-7 | | Lyme-Old Lyme High School - Tennis Courts | |
| MON 4/22 | 3:45 PM | Varsity | League | Normal | Home | Coginchaug | Loss | 1-6 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| TUE 4/23 | 3:45 PM | Varsity | League | Normal | Home | Cromwell | Loss | 2-5 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| WED 4/24 | 3:45 PM | Varsity | League | Normal | Away | Portland | Loss | 1-6 | | Portland High School - Tennis Courts | 12:00 PM |
| MON 4/29 | 3:45 PM | Varsity | League | Normal | Home | Westbrook | Loss | 1-6 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| THU 5/2 | 3:45 PM | Varsity | League | Normal | Away | North Branford | Loss | 3-4 | | North Branford High School - NBHS Tennis Courts | |
| FRI 5/3 | 3:45 PM | Varsity | League | Normal | Home | East Hampton | Loss | 2-5 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| MON 5/6 | 3:45 PM | Varsity | League | Normal | Home | Morgan | Loss | 0-7 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| TUE 5/7 | 3:45 PM | Varsity | League | Normal | Home | East Hampton | Win | 4-3 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| THU 5/9 | 3:45 PM | Varsity | League | Normal | Home | Portland | Loss | 1-6 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| FRI 5/10 | 3:45 PM | Varsity | League | Normal | Home | Valley Regional | Loss | 0-7 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| TUE 5/14 | 3:45 PM | Varsity | League | Normal | Away | Morgan | Loss | 0-7 | | Morgan School - Tennis Courts | |
| MON 5/20 | 9:00 AM | Varsity | Postseason | Normal | Away | Old Lyme | | | | Not Listed | |
| East Hampton | | |
| Westbrook | | |
| Cromwell | | |
| | |
| Portland | | |
| Old Saybrook | | |
| Morgan | | |
| North Branford | | |
| | |
| Coginchaug | | |
| Valley Regional | | |
| TUE 5/21 | 12:00 PM | Varsity | Postseason | Normal | Away | Old Lyme | | | | Lyme-Old Lyme High School - Tennis Courts | |
| East Hampton | | |
| | |
| Cromwell | | |
| Coginchaug | | |
| Portland | | |
| North Branford | | |
| Morgan | | |
| Old Saybrook | | |
| | |
| Westbrook | | |
| Valley Regional | | |