| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 3/26 | 3:45 PM | Varsity | Scrimmage | Normal | Away | | | | | Hamden Hall Country Day | 2:45 PM |
| MON 4/1 | 3:45 PM | Varsity | League | Normal | Home | Jonathan Law | Win | 5-2 | | North Haven Athletic Complex - Tennis Courts | |
| FRI 4/5 | 3:45 PM | Varsity | League | Normal | Home | Branford | Win | 5-2 | | North Haven Athletic Complex - Tennis Courts | |
| WED 4/10 | 3:45 PM | Varsity | League | Normal | Home | Lauralton Hall | Loss | 3-4 | | North Haven Athletic Complex - Tennis Courts | |
| FRI 4/12 | 1:00 PM | Varsity | League | Normal | Home | Lyman Hall | Win | 7-0 | | North Haven Health & Racquet - North Haven Health & Racquet | |
| MON 4/15 | 4:00 PM | Varsity | League | Normal | Away | Sacred Heart Academy | Win | 6-1 | | Albertus Magnus - Tennis Courts | 2:45 PM |
| TUE 4/16 | 3:45 PM | Varsity | League | Normal | Away | West Haven | Win | 7-0 | | West Haven High School - West Haven Tennis Courts | 2:30 PM |
| WED 4/17 | 3:45 PM | Varsity | League | Normal | Away | Amity | Loss | 1-6 | | Amity Regional High School - Tennis Courts | 2:30 PM |
| FRI 4/19 | 3:45 PM | Varsity | League | Normal | Away | Daniel Hand | Loss | 0-7 | | Polson Middle School, Madison - Polson Tennis Courts/DHHS Campus | 2:30 PM |
| TUE 4/23 | 3:45 PM | Varsity | Non-League | Normal | Away | Wilcox Tech | Win | 7-0 | | Wilcox Tech - Tennis Courts | 2:30 PM |
| WED 4/24 | 3:45 PM | Varsity | League | Normal | Away | Jonathan Law | Win | 4-3 | | Jonathan Law High School - Tennis Courts | 2:30 PM |
| THU 4/25 | 3:45 PM | Varsity | League | Normal | Home | West Haven | Win | 7-0 | | North Haven Athletic Complex - Tennis Courts | |
| MON 4/29 | 3:45 PM | Varsity | League | Normal | Away | Branford | Win | 4-3 | | Branford High School - Tennis Courts | 2:30 PM |
| FRI 5/3 | 3:45 PM | Varsity | League | Normal | Away | Lauralton Hall | Win | 5-2 | | Eisenhower Park - Eisenhower | 2:30 PM |
| MON 5/6 | 3:45 PM | Varsity | League | Normal | Away | Lyman Hall | Win | 7-0 | | Doolittle Park - Doolittle Tennis Courts | 2:30 PM |
| THU 5/9 | 3:45 PM | Varsity | League | Normal | Home | Amity | Loss | 1-6 | | North Haven Athletic Complex - Tennis Courts | |
| MON 5/13 | 3:45 PM | Varsity | League | Normal | Home | Daniel Hand | Loss | 0-7 | | North Haven Athletic Complex - Tennis Courts | |
| THU 5/16 | 2:30 PM | Varsity | League | Normal | Home | Sacred Heart Academy | Win | 6-1 | | North Haven Health & Racquet - North Haven Health & Racquet | |
| SUN 5/19 | 3:00 PM | Varsity | Postseason | Normal | Home | Lauralton Hall | Win | 4-3 | | North Haven Athletic Complex - Tennis Courts | |
| MON 5/20 | 3:30 PM | Varsity | Postseason | Normal | Away | Guilford | Loss | 1-6 | | Guilford High School - GHS Tennis Courts | |
| SAT 5/25 | 3:15 PM | Varsity | Postseason | Normal | Away | Brookfield | Win | 4-3 | | Brookfield High School - BHS Tennis Courts | 1:30 PM |
| TUE 5/28 | 2:15 PM | Varsity | Postseason | Normal | Away | New Canaan | Loss | 0-7 | | New Canaan HS - NCHS Tennis Courts | |