| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 4/1 | 3:45 PM | Varsity | League | Normal | Away | Lyman Hall | Win | 7-0 | | Doolittle Park - Doolittle Tennis Courts | |
| TUE 4/2 | Postponed | Varsity | Scrimmage | Postponed | Away | New Canaan | | | | New Canaan HS - NCHS Tennis Courts | |
| THU 4/4 | 3:45 PM | Varsity | League | Normal | Home | Notre Dame-West Haven | Win | 6-1 | | Fairfield University - Walsh Athletic Center - Tennis Courts | |
| SAT 4/6 | 10:00 AM | Varsity | Non-League | Normal | Away | Fairfield Ludlowe | Win | 5-2 | | Fairfield Ludlowe High School - Tennis Courts | |
| MON 4/8 | 4:45 PM | Varsity | League | Normal | Away | North Haven | Win | 7-0 | | North Haven Athletic Complex - Tennis Courts | |
| WED 4/10 | 3:45 PM | Varsity | League | Normal | Away | Daniel Hand | Win | 7-0 | | Polson Middle School, Madison - Polson Tennis Courts/DHHS Campus | |
| FRI 4/19 | 3:45 PM | Varsity | League | Normal | Home | | Win | 7-0 | | Fairfield University - Walsh Athletic Center - Tennis Courts | |
| SAT 4/20 | 1:00 PM | Varsity | League | Normal | Away | Cheshire | Win | 5-2 | | Cheshire High School - Tennis Courts | |
| MON 4/22 | 3:45 PM | Varsity | League | Normal | Away | Shelton | Win | 7-0 | | Shelton High School - Tennis Courts | |
| WED 4/24 | 3:45 PM | Varsity | League | Normal | Home | Lyman Hall | Win | 7-0 | | Fairfield University - Walsh Athletic Center - Tennis Courts | |
| THU 4/25 | 3:45 PM | Varsity | League | Normal | Away | Amity | Win | 4-3 | | Amity Regional High School - Tennis Courts | |
| MON 4/29 | 3:45 PM | Varsity | League | Normal | Home | Branford | Win | 7-0 | | Fairfield University - Walsh Athletic Center - Tennis Courts | |
| WED 5/1 | 3:45 PM | Varsity | League | Normal | Home | North Haven | Win | 7-0 | | Fairfield University - Walsh Athletic Center - Tennis Courts | |
| THU 5/2 | 3:45 PM | Varsity | League | Normal | Home | Shelton | Win | 7-0 | | Fairfield University - Walsh Athletic Center - Tennis Courts | |
| FRI 5/3 | 3:45 PM | Varsity | League | Normal | Home | Daniel Hand | Win | 5-2 | | Fairfield University - Walsh Athletic Center - Tennis Courts | |
| MON 5/6 | 3:45 PM | Varsity | League | Normal | Home | Amity | Win | 4-3 | | Fairfield University - Walsh Athletic Center - Tennis Courts | |
| WED 5/8 | 3:45 PM | Varsity | League | Normal | Away | Notre Dame-West Haven | Win | 6-1 | | U New Haven - UNH Tennis Courts | |
| FRI 5/10 | 3:45 PM | Varsity | League | Normal | Home | Cheshire | Win | 6-1 | | Fairfield University - Walsh Athletic Center - Tennis Courts | |
| SAT 5/18 | 10:00 AM | Varsity | Postseason | Normal | Home | Guilford | Win | 7-0 | | Fairfield University - Walsh Athletic Center - Tennis Courts | |
| MON 5/20 | 3:45 PM | Varsity | Postseason | Normal | Home | Daniel Hand | | | | Fairfield University - Walsh Athletic Center - Tennis Courts | |
| TUE 5/21 | 9:00 AM | Varsity | Postseason | Normal | Away | Amity | | | | Amity Regional High School - Tennis Courts | |
| SAT 5/25 | 11:00 AM | Varsity | League | Normal | Home | Fairfield Warde | Win | 6-1 | | Fairfield University - Walsh Athletic Center - Tennis Courts | |
| TUE 5/28 | 3:00 PM | Varsity | League | Normal | Home | Hall | Win | 5-1 | | Fairfield University - Walsh Athletic Center - Tennis Courts | |
| WED 5/29 | 3:45 PM | Varsity | League | Normal | Home | Staples | Loss | 3-4 | | Fairfield University - Walsh Athletic Center - Tennis Courts | |