| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 4/8 | 4:00 PM | Varsity | League | Normal | Away | Darien | Loss | 0-7 | | Darien High School - DHS Tennis Courts | 2:30 PM |
| TUE 4/9 | 4:00 PM | Varsity | League | Normal | Home | Wilton | Loss | 0-7 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| SAT 4/13 | 10:00 AM | Varsity | League | Normal | Away | New Canaan | Loss | 0-7 | | New Canaan HS - NCHS Tennis Courts | 8:30 AM |
| MON 4/15 | 4:00 PM | Varsity | League | Normal | Home | Staples | Loss | 0-7 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| TUE 4/16 | 10:00 AM | Varsity | League | Normal | Home | Ridgefield | Loss | 1-6 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| MON 4/22 | 4:00 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | Loss | 0-7 | | Fairfield Ludlowe High School - Tennis Courts | 2:30 PM |
| TUE 4/23 | 4:00 PM | Varsity | League | Normal | Home | Westhill | Loss | 0-7 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| THU 4/25 | 4:00 PM | Varsity | League | Normal | Home | Brien McMahon | Loss | 0-7 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| FRI 4/26 | 4:00 PM | Varsity | League | Normal | Away | St. Joseph | Loss | 1-6 | | St. Joseph High School - Tennis Courts | 2:30 PM |
| MON 4/29 | 4:00 PM | Varsity | League | Normal | Away | Danbury | Loss | 3-4 | | Danbury High School - DHS Tennis Courts | 2:30 PM |
| TUE 4/30 | 4:00 PM | Varsity | League | Normal | Home | Trumbull | Loss | 2-5 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| THU 5/2 | 4:00 PM | Varsity | League | Normal | Away | Fairfield Warde | Loss | 0-7 | | Fairfield Warde High School - Blake Courts | 2:30 PM |
| MON 5/6 | 4:00 PM | Varsity | League | Normal | Home | Greenwich | Loss | 0-7 | | Grassroots Tennis and Education - Grassroots Tennis Courts | |
| TUE 5/7 | 4:00 PM | Varsity | League | Normal | Away | Stamford | Loss | 1-6 | | Stamford High School - SHS Tennis Courts | 2:30 PM |
| THU 5/9 | 4:30 PM | Varsity | League | Normal | Away | Bridgeport Central | Win | 5-2 | | Bridgeport Central High School - Central High School Tennis Courts | 2:30 PM |