| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 3/25 | 3:30 PM | Varsity | Scrimmage | Normal | Away | Foran | Tied | 0-0 | | Foran High School - Richard A. Herman Memorial Tennis Courts | 2:10 PM - 1 Bus |
| SAT 3/30 | 10:30 AM | Varsity | League | Normal | Away | East Haven | Win | 7-0 | | East Haven High School - Tennis Court | 9:15 AM - 1 Bus |
| MON 4/1 | 3:45 PM | Varsity | League | Normal | Home | Fairfield Prep | Loss | 0-7 | | Doolittle Park - Doolittle Tennis Courts | |
| FRI 4/5 | 3:45 PM | Varsity | League | Normal | Away | Sheehan | Win | 4-3 | | Sheehan High School - Sheehan HS Tennis Courts | 2:30 PM - 1 Bus |
| MON 4/8 | 10:00 AM | Varsity | League | Normal | Home | Shelton | Win | 5-2 | | Doolittle Park - Doolittle Tennis Courts | |
| WED 4/10 | 1:00 PM | Varsity | League | Normal | Away | Cheshire | Loss | 0-7 | | Cheshire High School - Tennis Courts | 11:45 AM - 1 Bus |
| MON 4/15 | 3:45 PM | Varsity | League | Normal | Away | North Haven | Win | 4-3 | | North Haven Athletic Complex - Tennis Courts | 2:30 PM - 1 Bus |
| WED 4/17 | 3:45 PM | Varsity | League | Normal | Home | Wilbur Cross | Win | 4-3 | | Doolittle Park - Doolittle Tennis Courts | |
| MON 4/22 | 3:45 PM | Varsity | League | Normal | Home | East Haven | Win | 6-1 | | Doolittle Park - Doolittle Tennis Courts | |
| TUE 4/23 | 3:45 PM | Varsity | League | Normal | Away | Career Magnet | Win | 7-0 | | Edgewood Park - Tennis Courts | 2:30 PM - 1 Bus |
| WED 4/24 | 3:45 PM | Varsity | League | Normal | Away | Fairfield Prep | Loss | 0-7 | | Fairfield University - Walsh Athletic Center - Tennis Courts | 2:15 PM - 1 Bus |
| THU 4/25 | 3:30 PM | Varsity | Non-League | Normal | Away | Wilcox Tech | Win | 7-0 | | Wilcox Tech - Tennis Courts | 2:15 PM - 1 Bus |
| FRI 4/26 | 2:45 PM | Varsity | Non-League | Normal | Home | Wilcox Tech | Win | 7-0 | | Doolittle Park - Doolittle Tennis Courts | |
| MON 4/29 | 3:45 PM | Varsity | League | Normal | Away | West Haven | Loss | 0-7 | | West Haven High School - West Haven Tennis Courts | 2:20 PM - 1 Bus |
| WED 5/1 | 3:45 PM | Varsity | League | Normal | Away | Shelton | Loss | 2-5 | | Shelton High School - Tennis Courts | 2:10 PM - 1 Bus |
| THU 5/2 | 3:45 PM | Varsity | League | Normal | Home | West Haven | Win | 5-2 | | Doolittle Park - Doolittle Tennis Courts | |
| FRI 5/3 | 3:45 PM | Varsity | League | Normal | Home | Cheshire | Loss | 0-7 | | Doolittle Park - Doolittle Tennis Courts | |
| TUE 5/7 | 3:45 PM | Varsity | League | Normal | Home | Career Magnet | Win | 7-0 | | Doolittle Park - Doolittle Tennis Courts | |
| MON 5/13 | 5:00 PM | Varsity | League | Normal | Home | Sheehan | Loss | 1-6 | | Doolittle Park - Doolittle Tennis Courts | |
| TUE 5/14 | 3:45 PM | Varsity | League | Normal | Home | North Haven | Win | 4-3 | | Doolittle Park - Doolittle Tennis Courts | |
| MON 5/20 | 3:15 PM | Varsity | League | Normal | Away | Wilbur Cross | Loss | 2-5 | | Wilbur Cross High School - Wilbur Cross Tennis Courts | 2:10 PM - 1 Bus |
| FRI 5/24 | 11:00 AM | Varsity | Postseason | Normal | Home | New London | Win | 7-0 | | Doolittle Park - Doolittle Tennis Courts | |
| SAT 5/25 | 1:00 PM | Varsity | Postseason | Normal | Away | Lewis Mills | Loss | 1-6 | | Lewis Mills High School - Tennis Courts | 11:00 AM - 1 Bus |