| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 3/26 | 4:00 PM | Varsity | Scrimmage | Normal | Home | Seymour | | | | Trumbull High School - Tennis Courts | |
| WED 3/27 | 3:45 PM | Varsity | Scrimmage | Normal | Away | Shelton | Win | 4-3 | | Shelton High School - Tennis Courts | 3:00 PM - 1 Bus |
| MON 4/1 | 4:30 PM | Varsity | Scrimmage | Normal | Home | Joel Barlow | | | | Trumbull High School - Tennis Courts | |
| MON 4/8 | 5:00 PM | Varsity | League | Normal | Home | Westhill | Loss | 0-7 | | Trumbull High School - Tennis Courts | |
| TUE 4/9 | 4:00 PM | Varsity | League | Normal | Away | Danbury | Loss | 1-6 | | Danbury High School - DHS Tennis Courts | 2:30 PM - 1 Bus |
| TUE 4/9 | 4:00 PM | Junior Varsity | League | Normal | Away | Ridgefield | | | | Yanity Tennis Courts - Yanity Tennis Courts | 2:00 PM - 1 Bus |
| WED 4/10 | 4:00 PM | Junior Varsity | League | Normal | Home | St. Joseph | | | | Tashua Knolls Golf Course - Tennis Courts | |
| MON 4/15 | 4:00 PM | Varsity | League | Normal | Home | Brien McMahon | Loss | 2-5 | | Trumbull High School - Tennis Courts | |
| TUE 4/16 | Postponed | Junior Varsity | League | Postponed | Away | Wilton | | | | Wilton Middlebrook School - JV Tennis Courts | 2:45 PM - 1 Bus |
| TUE 4/16 | 4:00 PM | Varsity | League | Normal | Away | Wilton | Loss | 0-7 | | Wilton High School - Allen Meadow | 2:45 PM - 1 Bus |
| WED 4/17 | 3:00 PM | Varsity | League | Normal | Home | Fairfield Warde | Loss | 0-6 | | Trumbull High School - Tennis Courts | |
| MON 4/22 | 4:00 PM | Varsity | League | Normal | Home | Darien | Loss | 0-7 | | Trumbull High School - Tennis Courts | |
| TUE 4/23 | 4:00 PM | Junior Varsity | League | Normal | Home | Greenwich | | | | Tashua Knolls Golf Course - Tennis Courts | |
| TUE 4/23 | 4:00 PM | Varsity | League | Normal | Home | Greenwich | Loss | 0-7 | | Trumbull High School - Tennis Courts | |
| WED 4/24 | 5:00 PM | Varsity | League | Normal | Away | Bridgeport Central | Win | 6-1 | | Bridgeport Central High School - Central High School Tennis Courts | 3:45 PM - 1 Bus |
| WED 4/24 | 4:00 PM | Junior Varsity | League | Normal | Home | Darien | | | | Tashua Knolls Golf Course - Tennis Courts | |
| THU 4/25 | 4:00 PM | Varsity | League | Normal | Away | St. Joseph | Loss | 2-5 | | St. Joseph High School - Tennis Courts | 3:00 PM - 1 Bus |
| SAT 4/27 | 12:00 PM | Junior Varsity | League | Normal | Home | St. Joseph | | | | Trumbull High School - Tennis Courts | |
| MON 4/29 | 4:00 PM | Varsity | League | Normal | Away | Stamford | Loss | 3-4 | | Stamford High School - SHS Tennis Courts | 2:45 PM - 1 Bus |
| TUE 4/30 | 4:00 PM | Varsity | League | Normal | Away | Norwalk | Win | 5-2 | | Grassroots Tennis and Education - Grassroots Tennis Courts | 2:45 PM - 1 Bus |
| THU 5/2 | 4:00 PM | Varsity | League | Normal | Home | Staples | Loss | 0-7 | | Trumbull High School - Tennis Courts | |
| THU 5/2 | 4:00 PM | Junior Varsity | League | Normal | Home | Staples | | | | Tashua Knolls Golf Course - Tennis Courts | |
| MON 5/6 | 4:00 PM | Varsity | League | Normal | Home | Ridgefield | Loss | 2-5 | | Trumbull High School - Tennis Courts | |
| TUE 5/7 | 5:30 PM | Junior Varsity | League | Normal | Away | New Canaan | | | | New Canaan HS - NCHS Tennis Courts | |
| TUE 5/7 | 4:00 PM | Varsity | League | Normal | Away | New Canaan | Loss | 0-7 | | New Canaan HS - NCHS Tennis Courts | 2:45 PM - 1 Bus |
| WED 5/8 | 4:00 PM | Junior Varsity | League | Normal | Home | Ridgefield | | | | Tashua Knolls Golf Course - Tennis Courts | |
| THU 5/9 | 4:00 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | Loss | 0-7 | | Fairfield Ludlowe High School - Tennis Courts | 3:00 PM - 1 Bus |
| THU 5/9 | 4:00 PM | Junior Varsity | League | Normal | Away | Fairfield Ludlowe | | | | Dwight Elementary School - Tennis Courts | 3:00 PM - 1 Bus |
| TUE 5/14 | 4:30 PM | Junior Varsity | League | Normal | Away | Fairfield Warde | | | | Fairfield Woods - Tennis Courts | 4:00 PM - 1 Bus |