| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 4/8 | 5:00 PM | Varsity | League | Normal | Home | Darien | Loss | 1-6 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| TUE 4/9 | 4:00 PM | Varsity | League | Normal | Away | Wilton | Loss | 1-6 | | Wilton High School - Allen Meadow | 2:30 PM |
| SAT 4/13 | 10:00 AM | Varsity | League | Normal | Home | New Canaan | Loss | 1-6 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| MON 4/15 | 10:00 AM | Varsity | League | Normal | Away | Staples | Loss | 1-6 | | Staples High School - Staples Tennis Courts | 8:30 AM |
| TUE 4/16 | 10:00 AM | Varsity | League | Normal | Away | Ridgefield | Loss | 0-7 | | Ridgefield High School - RHS Tennis Courts | 8:30 AM |
| WED 4/17 | 4:00 PM | Varsity | League | Normal | Home | St. Joseph | Win | 3-0 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| MON 4/22 | 4:00 PM | Varsity | League | Normal | Home | Fairfield Ludlowe | Loss | 1-6 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| TUE 4/23 | 4:30 PM | Varsity | League | Normal | Away | Westhill | Loss | 0-7 | | Westhill High School - Westhill Tennis Courts | 2:30 PM |
| THU 4/25 | 4:00 PM | Varsity | League | Normal | Away | Brien McMahon | Loss | 2-5 | | Brien McMahon High School - Tennis Courts | 2:30 PM |
| MON 4/29 | 4:00 PM | Varsity | League | Normal | Home | Danbury | Loss | 3-4 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| TUE 4/30 | 4:00 PM | Varsity | League | Normal | Away | Trumbull | Loss | 0-7 | | Trumbull High School - Tennis Courts | 2:30 PM |
| THU 5/2 | 4:00 PM | Varsity | League | Normal | Home | Fairfield Warde | Loss | 2-5 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| MON 5/6 | 4:15 PM | Varsity | League | Normal | Away | Greenwich | Loss | 1-6 | | Greenwich High School - Tennis Courts | 2:30 PM |
| TUE 5/7 | 4:00 PM | Varsity | League | Normal | Home | Stamford | Loss | 3-4 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| MON 5/13 | 4:00 PM | Varsity | League | Normal | Home | Bridgeport Central | Win | 5-1 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |