| Tue 5/1 @ 3:45 PM | JV Baseball Game | vs. Fairfield Prep (Fairfield, CT) | | - |
| Wed 5/2 @ TBA | Varsity Baseball Game | @ Cheshire (CT)* | | - |
| Wed 5/2 @ 3:30 PM | Varsity Boys Volleyball Game | @ Oxford (CT) | | - |
| Wed 5/2 @ 3:45 PM | Varsity Softball Game | vs. Amity Regional (Woodbridge, CT)* | | - |
| Wed 5/2 @ 4:00 PM | JV Baseball Game | vs. Cheshire (CT) | | - |
| Thu 5/3 @ 4:00 PM | JV Baseball Game | vs. Cheshire (CT) | | - |
| Thu 5/3 @ 5:30 PM | Varsity Girls Lacrosse Game | vs. North Haven (CT)* | | - |
| Thu 5/3 @ 7:00 PM | Varsity Lacrosse Game | @ Wilbur Cross (New Haven, CT)* | | - |
| Fri 5/4 @ 3:45 PM | Freshman Baseball Game | vs. East Haven (CT) | | - |
| Fri 5/4 @ 4:00 PM | Varsity Softball Game | vs. Branford (CT) | | - |
| Sat 5/5 @ 10:00 AM | JV Baseball Game | @ East Haven (CT) | | - |
| Sat 5/5 @ 5:00 PM | Varsity Lacrosse Game | @ Westhill (Stamford, CT) | | - |
| Mon 5/7 @ TBA | Varsity Boys Volleyball Game | vs. Xavier (Middletown, CT)* | | - |
| Mon 5/7 @ TBA | Varsity Baseball Game | vs. Amity Regional (Woodbridge, CT)* | | - |
| Mon 5/7 @ 4:00 PM | Varsity Softball Game | @ Cheshire (CT)* | | - |
| Mon 5/7 @ 7:00 PM | Varsity Girls Lacrosse Game | vs. West Haven (CT)* | | - |
| Wed 5/9 @ 3:45 PM | Varsity Softball Game | vs. Lyman Hall (Wallingford, CT)* | | - |
| Wed 5/9 @ 7:00 PM | Varsity Lacrosse Game | vs. West Haven (CT)* | | - |
| Thu 5/10 @ TBA | Varsity Baseball Game | vs. East Haven (CT) | | - |
| Thu 5/10 @ 3:45 PM | JV Baseball Game | @ Sheehan (Wallingford, CT) | | - |
| Thu 5/10 @ 3:45 PM | Varsity Lacrosse Game | @ North Haven (CT)* | | - |
| Thu 5/10 @ 7:00 PM | Varsity Boys Volleyball Game | vs. Masuk (Monroe, CT) | | - |
| Fri 5/11 @ TBA | Varsity Baseball Game | vs. Lyman Hall (Wallingford, CT)* | | - |
| Fri 5/11 @ 3:45 PM | Varsity Softball Game | @ Sheehan (Wallingford, CT)* | | - |
| Fri 5/11 @ 3:45 PM | Freshman Baseball Game | vs. Lyman Hall (Wallingford, CT) | | - |
| Fri 5/11 @ 7:00 PM | Varsity Girls Lacrosse Game | vs. Sacred Heart Academy (Hamden, CT)* | | - |
| Sat 5/12 @ 10:00 AM | JV Baseball Game | @ Lyman Hall (Wallingford, CT) | | - |
| Sat 5/12 @ 10:30 AM | Freshman Baseball Game | vs. East Haven (CT) | | - |
| Mon 5/14 @ 3:45 PM | Varsity Softball Game | @ Hillhouse (New Haven, CT) | | - |
| Mon 5/14 @ 4:00 PM | JV Boys Volleyball Game | @ Southington (CT) | | - |
| Mon 5/14 @ 7:00 PM | Varsity Lacrosse Game | vs. Branford (CT)* | | - |
| Tue 5/15 @ 3:45 PM | Freshman Baseball Game | vs. Sheehan (Wallingford, CT) | | - |
| Tue 5/15 @ 7:00 PM | Varsity Girls Lacrosse Game | @ Guilford (CT)* | | - |
| Wed 5/16 @ TBA | Freshman Baseball Game | @ Notre Dame (West Haven, CT) | | - |
| Wed 5/16 @ TBA | Varsity Baseball Game | @ Notre Dame (West Haven, CT) | | - |
| Wed 5/16 @ 3:45 PM | Varsity Softball Game | vs. West Haven (CT) | | - |
| Wed 5/16 @ 7:00 PM | Varsity Girls Lacrosse Game | @ Watertown (CT) | | - |
| Thu 5/17 @ TBA | Varsity Baseball Game | vs. Sheehan (Wallingford, CT)* | | - |
| Thu 5/17 @ 3:45 PM | JV Baseball Game | vs. Notre Dame (West Haven, CT) | | - |
| Thu 5/17 @ 3:45 PM | JV Softball Game | vs. West Haven (CT) | | - |
| Thu 5/17 @ 4:00 PM | JV Softball Game | vs. West Haven (CT) | | - |
| Thu 5/17 @ 6:00 PM | Varsity Lacrosse Game | @ Amity Regional (Woodbridge, CT)* | | - |
| Fri 5/18 @ 3:45 PM | Freshman Baseball Game | vs. Wilbur Cross (New Haven, CT) | | - |
| Fri 5/18 @ 7:00 PM | Varsity Baseball Game | vs. Wilbur Cross (New Haven, CT) | | - |
| Fri 5/18 @ 7:30 PM | Varsity Girls Lacrosse Game | vs. Lewis Mills (Burlington, CT) | | - |
| Sat 5/19 @ 10:30 AM | JV Baseball Game | vs. Wilbur Cross (New Haven, CT) | | - |
| Sat 5/19 @ 10:30 AM | Freshman Baseball Game | vs. Sheehan (Wallingford, CT) | | - |
| Sat 5/19 @ 7:00 PM | Varsity Lacrosse Game | vs. Bethel (CT) | | - |
| Mon 5/21 @ 3:45 PM | Freshman Baseball Game | @ Foran (Milford, CT) | | - |
| Mon 5/21 @ 3:45 PM | Varsity Softball Game | @ Mercy (Middletown, CT) | | - |
| Mon 5/21 @ 6:00 PM | Varsity Girls Lacrosse Game | @ Cheshire (CT)** | | - |
| Tue 5/22 @ TBA | JV Baseball Game | @ Foran (Milford, CT) | | - |
| Tue 5/22 @ 3:45 PM | Freshman Baseball Game | @ Hand (Madison, CT) | | - |
| Tue 5/22 @ 3:45 PM | JV Baseball Game | @ Foran (Milford, CT) | | - |
| Wed 5/23 @ 3:30 PM | Varsity Baseball Game | @ Guilford (CT)*** | | - |
| Wed 5/23 @ 3:45 PM | Freshman Baseball Game | @ Foran (Milford, CT) | | - |
| Wed 5/23 @ 3:45 PM | JV Baseball Game | vs. Hand (Madison, CT) | | - |
| Wed 5/23 @ 7:45 PM | Varsity Baseball Game | vs. Foran (Milford, CT) | | - |
| Thu 5/24 @ 4:00 PM | Varsity Baseball Game | vs. Xavier (Middletown, CT)*** | | - |
| Sat 5/26 @ 12:00 PM | Varsity Baseball Game | @ Amity Regional (Woodbridge, CT)*** | | - |