| Tue 5/1 @ TBA | Varsity Lacrosse Game | vs. Warde (Fairfield, CT)* | | - |
| Wed 5/2 @ TBA | Varsity Softball Game | @ Westhill (Stamford, CT)* | | - |
| Wed 5/2 @ 4:00 PM | Varsity Baseball Game | vs. Westhill (Stamford, CT)* | | - |
| Wed 5/2 @ 6:00 PM | Varsity Girls Lacrosse Game | vs. Ridgefield (CT)* | | - |
| Fri 5/4 @ 4:00 PM | Varsity Baseball Game | vs. Ludlowe (Fairfield, CT)* | | - |
| Sat 5/5 @ TBA | Varsity Softball Game | @ Ludlowe (Fairfield, CT)* | | - |
| Sat 5/5 @ 4:00 PM | Varsity Softball Game | @ Ludlowe (Fairfield, CT)* | | - |
| Mon 5/7 @ TBA | Varsity Softball Game | vs. Staples (Westport, CT)* | | - |
| Mon 5/7 @ 4:00 PM | Varsity Baseball Game | @ Staples (Westport, CT)* | | - |
| Wed 5/9 @ 4:15 PM | Varsity Baseball Game | @ Wilton (CT)* | | - |
| Thu 5/10 @ TBA | Varsity Softball Game | vs. Wilton (CT)* | | - |
| Thu 5/10 @ 4:00 PM | Varsity Boys Volleyball Game | vs. Staples (Westport, CT)* | | - |
| Fri 5/11 @ TBA | Varsity Softball Game | vs. Trumbull (CT)* | | - |
| Fri 5/11 @ 6:00 PM | Varsity Baseball Game | @ Trumbull (CT)* | | - |
| Sat 5/12 @ 11:00 AM | Varsity Lacrosse Game | @ Greenwich (CT)* | | - |
| Mon 5/14 @ 4:00 PM | Varsity Baseball Game | @ New Canaan (CT)* | | - |
| Mon 5/14 @ 4:00 PM | Varsity Softball Game | vs. New Canaan (CT)* | | - |
| Mon 5/14 @ 5:30 PM | Varsity Boys Volleyball Game | vs. Ridgefield (CT)* | | - |
| Wed 5/16 @ TBA | Varsity Softball Game | @ Norwalk (CT)* | | - |
| Wed 5/16 @ 4:00 PM | Varsity Baseball Game | vs. Norwalk (CT)* | | - |
| Fri 5/18 @ TBA | Varsity Softball Game | @ Greenwich (CT)* | | - |
| Fri 5/18 @ 4:00 PM | Varsity Baseball Game | vs. Greenwich (CT)* | | - |
| Wed 5/23 @ 4:00 PM | Varsity Baseball Game | @ Greenwich (CT)*** | | - |
| Tue 5/29 @ TBA | Varsity Softball Game | @ Ridgefield (CT)*** | | - |
| Tue 5/29 @ 3:30 PM | Varsity Baseball Game | vs. Southington (CT)*** | | - |
| Wed 5/30 @ 4:00 PM | Varsity Softball Game | @ Ludlowe (Fairfield, CT)*** | | - |