| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 4/6 | 10:00 AM | Varsity | Non-League | Normal | Away | East Haven | Loss | 1-6 | | East Haven High School - Tennis Court | |
| MON 4/8 | 3:45 PM | Varsity | League | Normal | Away | Abbott Tech | Loss | 0-7 | | Abbott V-T School - Abbott Tech Tennis Complex | |
| WED 4/10 | 11:00 AM | Varsity | Non-League | Normal | Away | Platt | Loss | 0-7 | | Platt High School - Tennis Court | |
| SAT 4/13 | 10:00 AM | Varsity | Non-League | Normal | Away | Pomperaug | Loss | 0-7 | | Edgewood Bath and Tennis Club - Edgewood Bath and Tennis Club | |
| MON 4/15 | 3:45 PM | Varsity | Non-League | Normal | Home | Plainville | Loss | 3-4 | | Wilcox Tech - Tennis Courts | |
| TUE 4/16 | 3:45 PM | Varsity | Non-League | Normal | Away | Jonathan Law | Loss | 0-7 | | Jonathan Law High School - Tennis Courts | |
| WED 4/17 | 3:45 PM | Varsity | League | Normal | Home | Platt Tech | Loss | 1-6 | | Wilcox Tech - Tennis Courts | |
| FRI 4/19 | 3:45 PM | Varsity | Non-League | Normal | Away | North Haven | Loss | 1-6 | | North Haven Athletic Complex - Tennis Courts | |
| MON 4/22 | 3:45 PM | Varsity | Non-League | Normal | Home | Platt | Loss | 0-7 | | Wilcox Tech - Tennis Courts | |
| WED 4/24 | 3:45 PM | Varsity | Non-League | Normal | Home | New Britain | Loss | 3-4 | | Wilcox Tech - Tennis Courts | |
| THU 4/25 | 3:30 PM | Varsity | Non-League | Normal | Home | Lyman Hall | Loss | 0-7 | | Wilcox Tech - Tennis Courts | |
| FRI 4/26 | 2:45 PM | Varsity | Non-League | Normal | Away | Lyman Hall | Loss | 0-7 | | Doolittle Park - Doolittle Tennis Courts | |
| MON 4/29 | 3:45 PM | Varsity | League | Normal | Home | Grasso Tech | Loss | 3-4 | | Wilcox Tech - Tennis Courts | |
| WED 5/1 | 3:45 PM | Varsity | Non-League | Normal | Home | Pomperaug | Loss | 0-7 | | Wilcox Tech - Tennis Courts | |
| MON 5/6 | 3:45 PM | Varsity | League | Normal | Away | Platt Tech | Loss | 2-5 | | Eisenhower Park - Eisenhower | |
| TUE 5/7 | 3:45 PM | Varsity | Non-League | Normal | Away | New Britain | Loss | 2-5 | | New Britain High School - tennis courts | |
| THU 5/9 | 3:45 PM | Varsity | Non-League | Normal | Home | East Haven | Win | 4-3 | | Wilcox Tech - Tennis Courts | |
| MON 5/13 | 3:45 PM | Varsity | League | Normal | Home | Abbott Tech | Loss | 2-5 | | Wilcox Tech - Tennis Courts | |
| TUE 5/14 | 3:15 PM | Varsity | League | Normal | Away | Grasso Tech | Loss | 2-5 | | Washington Park - Washington Park Tennis Courts | |
| TUE 5/21 | 2:00 PM | Varsity | League | Normal | Home | Jonathan Law | Loss | 0-7 | | Wilcox Tech - Tennis Courts | |
| WED 5/22 | 9:00 AM | Varsity | Postseason | Normal | Home | Abbott Tech | | | | Wesleyan - Middletown Tennis Courts | |
| Platt Tech | | |
| Grasso Tech | | |