| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 4/1 | 3:45 PM | Varsity | League | Normal | Home | Westbrook | Loss | 0-7 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| MON 4/8 | 10:30 AM | Varsity | League | Normal | Away | Valley Regional | Loss | 2-5 | | Valley Regional High School - Tennis Courts | |
| TUE 4/16 | 4:00 PM | Varsity | League | Normal | Away | Old Saybrook | Win | 7-0 | | Old Saybrook High School - Old Saybrook Tennis Courts | |
| FRI 4/19 | 3:45 PM | Varsity | League | Normal | Home | Old Lyme | Loss | 3-4 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| MON 4/22 | 4:00 PM | Varsity | League | Normal | Away | Coginchaug | Win | 5-2 | | Coginchaug Regional High School - Tennis Courts @ CRHS | |
| MON 4/29 | 3:45 PM | Varsity | League | Normal | Away | Westbrook | Loss | 3-4 | | Westbrook High School - Westbrook HS / MS Tennis Courts | |
| FRI 5/3 | 3:45 PM | Varsity | League | Normal | Home | East Hampton/Portland | Loss | 3-4 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| SAT 5/4 | 10:00 AM | Varsity | League | Normal | Home | Cromwell | Win | 4-3 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| MON 5/6 | 3:45 PM | Varsity | League | Normal | Away | Morgan | Win | 4-3 | | Morgan School - Tennis Courts | |
| TUE 5/7 | 3:45 PM | Varsity | League | Normal | Home | East Hampton/Portland | Win | 5-2 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| THU 5/9 | 3:45 PM | Varsity | Non-League | Normal | Away | Old Lyme | Loss | 2-5 | | Lyme-Old Lyme High School - Tennis Courts | |
| MON 5/13 | 3:45 PM | Varsity | Non-League | Normal | Home | Valley Regional | Loss | 3-4 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| TUE 5/14 | 4:00 PM | Varsity | Non-League | Normal | Home | Windsor Locks | Win | 7-0 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| MON 5/20 | 9:00 AM | Varsity | Postseason | Normal | Away | Westbrook | | | | Not Listed | |
| | |
| Valley Regional | | |
| Old Saybrook | | |
| North Branford | | |
| Old Lyme | | |
| East Hampton/Portland | | |
| Morgan | | |
| Cromwell | | |
| Coginchaug | | |
| TUE 5/21 | 4:00 PM | Varsity | Postseason | Normal | Away | Coginchaug | | | | Morgan School - Tennis Courts | |
| Cromwell | | |
| Morgan | | |
| East Hampton/Portland | | |
| Old Lyme | | |
| North Branford | | |
| Old Saybrook | | |
| Valley Regional | | |
| | |
| | |
| WED 5/22 | 1:00 PM | Varsity | League | Normal | Home | Morgan | Win | 5-2 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | |
| FRI 5/24 | 4:30 PM | Varsity | Postseason | Normal | Away | Stonington | Loss | 0-7 | | Stonington High School - SHS Tennis Courts | |