| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 3/22 | 3:30 PM | Varsity | Scrimmage | Normal | Away | Weston | | | | Weston High School - WHS Tennis Courts | 3:00 PM |
| SAT 3/30 | 11:00 AM | Varsity | League | Normal | Away | Branford | Win | 6-1 | | Branford High School - Tennis Courts | 9:30 AM |
| MON 4/8 | 5:00 PM | Varsity | League | Normal | Away | Ridgefield | Win | 6-1 | | Ridgefield High School - RHS Tennis Courts | 3:15 PM - v/jv going together |
| TUE 4/9 | 4:00 PM | Varsity | League | Normal | Home | New Canaan | Loss | 1-6 | | Staples High School - Staples Tennis Courts | |
| MON 4/15 | 4:00 PM | Varsity | League | Normal | Away | Norwalk | Win | 7-0 | | Grassroots Tennis and Education - Grassroots Tennis Courts | 3:00 PM |
| TUE 4/16 | 4:30 PM | Varsity | League | Normal | Home | Stamford | Win | 7-0 | | Staples High School - Staples Tennis Courts | |
| WED 4/17 | 10:00 AM | Varsity | League | Normal | Away | Brien McMahon | Win | 7-0 | | Brien McMahon High School - Tennis Courts | 3:00 PM |
| MON 4/22 | 3:30 PM | Varsity | League | Normal | Away | Greenwich | Loss | 1-6 | | Greenwich High School - Tennis Courts | 2:15 PM - jv/ v goin together |
| TUE 4/23 | 4:00 PM | Varsity | League | Normal | Away | Wilton | Loss | 1-6 | | Wilton High School - Tennis Courts | 3:00 PM - jv/v going together |
| THU 4/25 | 4:00 PM | Varsity | League | Normal | Home | Bridgeport Central | Win | 7-0 | | Staples High School - Staples Tennis Courts | |
| MON 4/29 | 4:00 PM | Varsity | League | Normal | Home | Fairfield Warde | Win | 6-1 | | Staples High School - Staples Tennis Courts | |
| TUE 4/30 | 4:00 PM | Varsity | League | Normal | Home | Fairfield Ludlowe | Loss | 1-6 | | Staples High School - Staples Tennis Courts | |
| WED 5/1 | 4:00 PM | Varsity | League | Normal | Home | Darien | Loss | 3-4 | | Staples High School - Staples Tennis Courts | |
| THU 5/2 | 4:00 PM | Varsity | League | Normal | Away | Trumbull | Win | 7-0 | | Trumbull High School - Tennis Courts | 2:30 PM - jv/v going together |
| MON 5/6 | 4:00 PM | Varsity | League | Normal | Away | Danbury | Win | 6-1 | | Danbury High School - DHS Tennis Courts | 2:30 PM |
| TUE 5/7 | 4:00 PM | Varsity | League | Normal | Home | St. Joseph | Win | 6-1 | | Staples High School - Staples Tennis Courts | |
| THU 5/9 | 4:30 PM | Varsity | League | Normal | Home | Westhill | Win | 4-3 | | Staples High School - Staples Tennis Courts | |
| MON 5/13 | 4:00 PM | Varsity | Postseason | Normal | Away | Darien | | | | Darien High School - DHS Tennis Courts | 2:30 PM |
| FRI 5/24 | 12:00 PM | Varsity | Postseason | Normal | Home | New Britain | Win | 7-0 | | Staples High School - Staples Tennis Courts | |
| SAT 5/25 | 12:00 PM | Varsity | Tournament | Normal | Away | Cheshire | Win | 4-3 | | Cheshire High School - Tennis Courts | 12:00 PM |
| TUE 5/28 | 3:00 PM | Varsity | Tournament | Normal | Away | Maloney | Win | 7-0 | | Maloney High School - Tennis Courts | 12:30 PM |
| WED 5/29 | 3:30 PM | Varsity | Postseason | Normal | Away | South Windsor | Win | 6-1 | | South Windsor High School - Wapping Tennis Courts | 12:00 PM |
| THU 5/30 | 3:30 PM | Varsity | Postseason | Normal | Home | Greenwich | Loss | 0-4 | | Wilton High School - Wilton HS tennis courts | |