| Tue 5/1 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Westhill (Stamford, CT) | | - |
| Wed 5/2 @ TBA | Varsity Baseball Game | vs. Ridgefield (CT)* | | - |
| Wed 5/2 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Warde (Fairfield, CT)* | | - |
| Wed 5/2 @ 4:00 PM | Varsity Softball Game | @ Ridgefield (CT)* | | - |
| Thu 5/3 @ 4:00 PM | Varsity Lacrosse Game | vs. North Haven (CT) | | - |
| Fri 5/4 @ 4:00 PM | Freshman Baseball Game | vs. New Canaan (CT) | | - |
| Fri 5/4 @ 4:00 PM | Varsity Baseball Game | @ New Canaan (CT)* | | - |
| Fri 5/4 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Norwalk (CT)* | | - |
| Fri 5/4 @ 4:00 PM | Varsity Softball Game | vs. New Canaan (CT)* | | - |
| Fri 5/4 @ 4:00 PM | JV Baseball Game | @ New Canaan (CT) | | - |
| Sat 5/5 @ TBA | Varsity Lacrosse Game | @ Trumbull (CT)* | | - |
| Mon 5/7 @ TBA | Varsity Girls Lacrosse Game | vs. Bunnell (Stratford, CT) | | - |
| Mon 5/7 @ TBA | Varsity Baseball Game | vs. Norwalk (CT)* | | - |
| Tue 5/8 @ 4:00 PM | Varsity Lacrosse Game | vs. Staples (Westport, CT)* | | - |
| Tue 5/8 @ 4:00 PM | Varsity Baseball Game | @ Bassick (Bridgeport, CT)* | | - |
| Wed 5/9 @ 4:00 PM | Varsity Baseball Game | vs. Darien (CT)* | | - |
| Thu 5/10 @ TBA | Varsity Girls Lacrosse Game | vs. McMahon (Norwalk, CT)* | | - |
| Thu 5/10 @ TBA | Varsity Softball Game | @ Darien (CT)* | | - |
| Thu 5/10 @ 4:00 PM | Varsity Lacrosse Game | @ St. Joseph (Trumbull, CT)* | | - |
| Thu 5/10 @ 4:00 PM | JV Baseball Game | @ St. Joseph (Trumbull, CT) | | - |
| Thu 5/10 @ 4:00 PM | Freshman Baseball Game | @ Darien (CT) | | - |
| Thu 5/10 @ 4:00 PM | Varsity Softball Game | vs. St. Joseph (Trumbull, CT)* | | - |
| Fri 5/11 @ 3:00 PM | Varsity Baseball Game | @ St. Joseph (Trumbull, CT)* | | - |
| Fri 5/11 @ 3:00 PM | JV Baseball Game | @ St. Joseph (Trumbull, CT) | | - |
| Sat 5/12 @ TBA | Varsity Lacrosse Game | @ New Canaan (CT)* | | - |
| Mon 5/14 @ TBA | Varsity Lacrosse Game | @ Ridgefield (CT)* | | - |
| Mon 5/14 @ TBA | Varsity Softball Game | @ Warde (Fairfield, CT)* | | - |
| Mon 5/14 @ 4:00 PM | Varsity Baseball Game | vs. Warde (Fairfield, CT)* | | - |
| Tue 5/15 @ 7:00 PM | Varsity Girls Lacrosse Game | vs. Trumbull (CT)* | | - |
| Wed 5/16 @ TBA | Varsity Softball Game | vs. Bassick (Bridgeport, CT)* | | - |
| Wed 5/16 @ 4:00 PM | Varsity Baseball Game | @ Bassick (Bridgeport, CT)* | | - |
| Wed 5/16 @ 4:00 PM | Varsity Lacrosse Game | vs. Darien (CT)* | | - |
| Wed 5/16 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Bethel (CT) | | - |
| Fri 5/18 @ TBA | Varsity Softball Game | vs. Harding (Bridgeport, CT)* | | - |
| Fri 5/18 @ 4:00 PM | Varsity Baseball Game | @ Harding (Bridgeport, CT)* | | - |
| Tue 5/29 @ TBA | Varsity Softball Game | @ South Windsor (CT)*** | | - |
| Tue 5/29 @ 3:30 PM | Varsity Baseball Game | @ Trumbull (CT)*** | | - |
| Tue 5/29 @ 3:30 PM | Varsity Football Practice | Practice | 2 hrs 30 mins | - |
| Wed 5/30 @ 4:00 PM | Varsity Softball Game | @ Southington (CT)** | | - |