| Wed 5/2 @ 3:45 PM | Varsity Softball Game | vs. Greenwich Academy (Greenwich, CT) | | - |
| Sat 5/5 @ TBA | Varsity Baseball Game | @ Hotchkiss (Lakeville, CT) | | - |
| Sat 5/5 @ 11:30 AM | JV Baseball Game | @ Hamden Hall Country Day (Hamden, CT) | | - |
| Sat 5/5 @ 3:30 PM | Varsity Softball Game | @ Canterbury (New Milford, CT) | | - |
| Sat 5/5 @ 4:00 PM | Varsity Lacrosse Game | @ Masters (Dobbs Ferry, NY)* | | - |
| Wed 5/9 @ 3:00 PM | Varsity Softball Game | @ Miss Porter's (Farmington, CT) | | - |
| Fri 5/11 @ 4:30 PM | Varsity Baseball Game | vs. Gunnery (Washington, CT) | | - |
| Sat 5/12 @ 1:30 PM | JV Baseball Game | vs. Hopkins (New Haven, CT) | | - |
| Sat 5/12 @ 3:00 PM | Varsity Softball Game | vs. Williston Northampton (Easthampton, MA) | | - |
| Mon 5/14 @ 4:30 PM | Varsity Softball Game | vs. Loomis Chaffee (Windsor, CT) | | - |
| Mon 5/14 @ 4:30 PM | JV Baseball Game | vs. Suffield Academy (Suffield, CT) | | - |
| Wed 5/16 @ 3:00 PM | JV Baseball Game | @ Westminster (Simsbury, CT) | | - |
| Wed 5/16 @ 3:00 PM | Varsity Baseball Game | vs. Westminster (Simsbury, CT)* | | - |
| Wed 5/16 @ 5:00 PM | Varsity Softball Game | @ Suffield Academy (Suffield, CT) | | - |
| Thu 5/17 @ 4:30 PM | Varsity Baseball Game | @ Choate Rosemary Hall (Wallingford, CT)* | | - |
| Sat 5/19 @ 12:00 PM | Varsity Lacrosse Game | @ Williston Northampton (Easthampton, MA)* | | - |
| Sat 5/19 @ 2:30 PM | Varsity Baseball Game | vs. Loomis Chaffee (Windsor, CT) | | - |
| Sat 5/19 @ 2:30 PM | JV Baseball Game | @ Loomis Chaffee (Windsor, CT) | | - |
| Mon 5/21 @ 4:30 PM | Varsity Lacrosse Game | vs. Hamden Hall Country Day (Hamden, CT)*** | | - |