| Tue 5/1 @ 6:00 PM | Varsity Lacrosse Game | vs. Trumbull (CT)* | | - |
| Wed 5/2 @ TBA | Varsity Baseball Game | @ Stamford (CT)* | | - |
| Wed 5/2 @ 4:00 PM | Varsity Softball Game | vs. Stamford (CT)* | | - |
| Wed 5/2 @ 5:30 PM | Varsity Boys Volleyball Game | @ Staples (Westport, CT)* | | - |
| Wed 5/2 @ 6:00 PM | Varsity Girls Lacrosse Game | @ Danbury (CT)* | | - |
| Fri 5/4 @ 4:00 PM | Varsity Softball Game | vs. McMahon (Norwalk, CT)* | | - |
| Fri 5/4 @ 4:00 PM | Freshman Baseball Game | @ St. Joseph (Trumbull, CT) | | - |
| Fri 5/4 @ 5:30 PM | Varsity Boys Volleyball Game | vs. New Canaan (CT)* | | - |
| Sat 5/5 @ TBA | Varsity Baseball Game | @ McMahon (Norwalk, CT)* | | - |
| Sat 5/5 @ 3:00 PM | Varsity Girls Lacrosse Game | vs. Newtown (CT) | | - |
| Sat 5/5 @ 6:00 PM | Varsity Lacrosse Game | vs. McMahon (Norwalk, CT)* | | - |
| Mon 5/7 @ TBA | Varsity Softball Game | @ Trumbull (CT)* | | - |
| Mon 5/7 @ 4:00 PM | Varsity Softball Game | @ Trumbull (CT)* | | - |
| Mon 5/7 @ 4:00 PM | JV Baseball Game | vs. Trumbull (CT) | | - |
| Mon 5/7 @ 4:00 PM | Varsity Baseball Game | vs. Trumbull (CT)* | | - |
| Mon 5/7 @ 5:30 PM | Varsity Boys Volleyball Game | vs. Warde/Ludlowe (Fairfield, CT)* | | - |
| Tue 5/8 @ 4:00 PM | Varsity Softball Game | vs. McMahon (Norwalk, CT)* | | - |
| Tue 5/8 @ 7:00 PM | Varsity Lacrosse Game | vs. Darien (CT)* | | - |
| Wed 5/9 @ 4:00 PM | Freshman Baseball Game | @ Notre Dame Catholic (Fairfield, CT) | | - |
| Wed 5/9 @ 4:00 PM | Varsity Softball Game | @ Warde (Fairfield, CT)* | | - |
| Wed 5/9 @ 5:30 PM | Varsity Boys Volleyball Game | @ Greenwich (CT)* | | - |
| Thu 5/10 @ TBA | Varsity Softball Game | @ Warde (Fairfield, CT)* | | - |
| Thu 5/10 @ TBA | Varsity Baseball Game | vs. Warde (Fairfield, CT)* | | - |
| Thu 5/10 @ 4:00 PM | Varsity Lacrosse Game | @ New Canaan (CT)* | | - |
| Thu 5/10 @ 6:00 PM | Varsity Girls Lacrosse Game | vs. Trumbull (CT)* | | - |
| Fri 5/11 @ TBA | Varsity Softball Game | @ Ludlowe (Fairfield, CT)* | | - |
| Fri 5/11 @ TBA | Varsity Baseball Game | vs. Ludlowe (Fairfield, CT)* | | - |
| Fri 5/11 @ After JV | Varsity Boys Volleyball Game | @ Darien (CT)* | | - |
| Fri 5/11 @ 4:00 PM | Varsity Softball Game | @ Ludlowe (Fairfield, CT)* | | - |
| Sat 5/12 @ 1:00 PM | Varsity Lacrosse Game | @ St. Joseph (Trumbull, CT)* | | - |
| Sat 5/12 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Westhill (Stamford, CT) | | - |
| Mon 5/14 @ TBA | Varsity Softball Game | vs. Staples (Westport, CT)* | | - |
| Mon 5/14 @ TBA | Varsity Lacrosse Game | vs. Stamford (CT)* | | - |
| Mon 5/14 @ TBA | Varsity Baseball Game | @ Staples (Westport, CT)* | | - |
| Mon 5/14 @ 4:00 PM | Varsity Softball Game | vs. Staples (Westport, CT)* | | - |
| Mon 5/14 @ 5:30 PM | Varsity Boys Volleyball Game | @ Danbury (CT)* | | - |
| Mon 5/14 @ 6:00 PM | Varsity Girls Lacrosse Game | @ New Milford (CT) | | - |
| Tue 5/15 @ TBA | Varsity Girls Lacrosse Game | @ Staples (Westport, CT)* | | - |
| Wed 5/16 @ 4:00 PM | Varsity Softball Game | vs. St. Joseph (Trumbull, CT)* | | - |
| Wed 5/16 @ 4:15 PM | Varsity Baseball Game | @ St. Joseph (Trumbull, CT)* | | - |
| Wed 5/16 @ 5:30 PM | Varsity Boys Volleyball Game | vs. St. Joseph (Trumbull, CT)* | | - |
| Thu 5/17 @ TBA | Varsity Baseball Game | @ Westhill (Stamford, CT)* | | - |
| Thu 5/17 @ TBA | Varsity Softball Game | vs. Westhill (Stamford, CT)* | | - |
| Thu 5/17 @ 4:00 PM | Varsity Softball Game | vs. Westhill (Stamford, CT)* | | - |
| Thu 5/17 @ 5:30 PM | Varsity Boys Volleyball Game | @ Masuk (Monroe, CT) | | - |
| Fri 5/18 @ 5:00 PM | Varsity Girls Lacrosse Game | @ Greenwich (CT)*** | | - |
| Sat 5/19 @ 11:30 AM | Varsity Lacrosse Game | vs. Staples (Westport, CT)** | | - |
| Tue 5/22 @ 7:30 PM | Varsity Lacrosse Game | @ Darien (CT)** | | - |
| Wed 5/23 @ 5:00 PM | Varsity Boys Volleyball Game | @ Greenwich (CT)*** | | - |
| Fri 5/25 @ 7:00 PM | Varsity Lacrosse Game | @ New Canaan (CT)** | | - |
| Fri 5/25 @ 7:00 PM | Varsity Boys Volleyball Game | @ Darien (CT)*** | | - |
| Tue 5/29 @ TBA | Varsity Softball Game | @ Danbury (CT)*** | | - |
| Wed 5/30 @ TBA | Varsity Baseball Game | @ Staples (Westport, CT)*** | | - |
| Wed 5/30 @ 4:30 PM | Varsity Lacrosse Game | vs. Newington (CT)** | | - |
| Thu 5/31 @ 5:00 PM | Varsity Boys Volleyball Game | vs. Xavier (Middletown, CT)** | | - |