| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 3/26 | 3:45 PM | Varsity | Scrimmage | Normal | Away | Daniel Hand | | | | Polson Middle School, Madison - Polson Tennis Courts/DHHS Campus | 2:30 PM - 1 Bus |
| MON 4/1 | 3:45 PM | Varsity | League | Normal | Home | Coginchaug | Win | 7-0 | | Valley Regional High School - Tennis Courts | |
| MON 4/8 | 10:30 AM | Varsity | League | Normal | Home | Haddam Killingworth | Win | 5-2 | | Valley Regional High School - Tennis Courts | |
| MON 4/15 | 4:00 PM | Varsity | League | Normal | Away | Cromwell | Loss | 3-4 | | Watrous park - Watrous park | 2:35 PM - 1 Bus |
| TUE 4/16 | 3:45 PM | Varsity | League | Normal | Home | East Hampton/Portland | Win | 5-2 | | Valley Regional High School - Tennis Courts | |
| FRI 4/19 | 3:45 PM | Varsity | League | Normal | Home | Old Saybrook | Win | 7-0 | | Valley Regional High School - Tennis Courts | |
| MON 4/22 | 4:00 PM | Varsity | League | Normal | Away | Old Lyme | Win | 4-3 | | Lyme-Old Lyme High School - Tennis Courts | 3:00 PM - 1 Bus |
| WED 4/24 | 3:45 PM | Varsity | League | Normal | Away | Westbrook | Loss | 3-4 | | Westbrook High School - Westbrook HS / MS Tennis Courts | 2:35 PM - 1 Bus |
| MON 4/29 | 3:45 PM | Varsity | League | Normal | Away | Morgan | Loss | 3-4 | | Morgan School - Tennis Courts | 2:30 PM - 1 Bus |
| WED 5/1 | 3:45 PM | Varsity | League | Normal | Home | Old Lyme | Win | 5-2 | | Valley Regional High School - Tennis Courts | |
| FRI 5/3 | 3:45 PM | Varsity | Non-League | Normal | Home | Westbrook | Loss | 3-4 | | Valley Regional High School - Tennis Courts | |
| TUE 5/7 | 3:45 PM | Varsity | League | Normal | Home | Morgan | Win | 4-3 | | Valley Regional High School - Tennis Courts | |
| FRI 5/10 | 3:45 PM | Varsity | League | Normal | Away | Coginchaug | Win | 6-1 | | Coginchaug Regional High School - Tennis Courts @ CRHS | 2:35 PM - 1 Bus |
| MON 5/13 | 3:45 PM | Varsity | Non-League | Normal | Away | Haddam Killingworth | Win | 4-3 | | Haddam Killingworth High School (HK) - HKHS Tennis Courts | 2:35 PM - 1 Bus |
| MON 5/20 | 9:00 AM | Varsity | Postseason | Normal | Away | Haddam Killingworth | | | | Not Listed | |
| Coginchaug | | |
| Morgan | | |
| East Hampton/Portland | | |
| Cromwell | | |
| Westbrook | | |
| North Branford | | |
| Old Lyme | | |
| Old Saybrook | | |
| | |
| TUE 5/21 | 4:00 PM | Varsity | Postseason | Normal | Away | | | | | Morgan School - Tennis Courts | |
| | |
| Old Saybrook | | |
| Old Lyme | | |
| North Branford | | |
| Cromwell | | |
| East Hampton/Portland | | |
| Morgan | | |
| Coginchaug | | |
| Haddam Killingworth | | |
| SAT 5/25 | 2:00 PM | Varsity | Postseason | Normal | Away | Old Lyme | Loss | 1-6 | | Lyme-Old Lyme High School - Tennis Courts | 12:45 PM - 1 Bus |