| Wed 5/2 @ 2:30 PM | Freshman Baseball Game | vs. Berkshire School (Sheffield, MA) | | - |
| Wed 5/2 @ 3:00 PM | Varsity Baseball Game | @ Trinity-Pawling (Pawling, NY)* | | - |
| Thu 5/3 @ 3:45 PM | JV Baseball Game | vs. Avon (CT) | | - |
| Fri 5/4 @ 4:30 PM | Varsity Baseball Game | @ Taft (Watertown, CT)* | | - |
| Sat 5/5 @ TBA | Varsity Baseball Game | vs. Westminster (Simsbury, CT) | | - |
| Sat 5/5 @ 3:15 PM | JV Baseball Game | @ Hopkins (New Haven, CT) | | - |
| Mon 5/7 @ 3:45 PM | Freshman Baseball Game | vs. Avon (CT) | | - |
| Wed 5/9 @ 2:30 PM | JV Baseball Game | vs. Loomis Chaffee (Windsor, CT) | | - |
| Wed 5/9 @ 3:00 PM | Varsity Baseball Game | @ Loomis Chaffee (Windsor, CT)* | | - |
| Thu 5/10 @ 4:30 PM | Varsity Baseball Game | @ Loomis Chaffee (Windsor, CT)* | | - |
| Sat 5/12 @ TBA | Varsity Baseball Game | vs. Hotchkiss (Lakeville, CT)* | | - |
| Sat 5/12 @ TBA | Varsity Lacrosse Game | vs. Deerfield Academy (Deerfield, MA)* | | - |
| Sat 5/12 @ 2:30 PM | Freshman Baseball Game | @ Brunswick (Greenwich, CT) | | - |
| Mon 5/14 @ 4:30 PM | Varsity Baseball Game | vs. Suffield Academy (Suffield, CT) | | - |
| Wed 5/16 @ 2:30 PM | Freshman Baseball Game | vs. Berkshire School (Sheffield, MA) | | - |
| Wed 5/16 @ 3:00 PM | Varsity Baseball Game | @ Deerfield Academy (Deerfield, MA) | | - |
| Wed 5/16 @ 3:00 PM | Varsity Lacrosse Game | vs. Taft (Watertown, CT)* | | - |
| Fri 5/18 @ 3:45 PM | Freshman Baseball Game | vs. Avon (CT) | | - |
| Sat 5/19 @ 1:00 PM | Varsity Lacrosse Game | @ Salisbury School (Salisbury, CT)* | | - |
| Sat 5/19 @ 2:30 PM | Freshman Baseball Game | vs. Trinity-Pawling (Pawling, NY) | | - |
| Sat 5/19 @ 2:30 PM | Varsity Baseball Game | vs. Trinity-Pawling (Pawling, NY)* | | - |
| Tue 5/22 @ 3:45 PM | Freshman Baseball Game | vs. Rumsey Hall (Washington Depot, CT) | | - |
| Wed 5/23 @ TBA | Varsity Baseball Game | vs. Choate Rosemary Hall (Wallingford, CT)*** | | - |
| Wed 5/23 @ 2:30 PM | Freshman Baseball Game | vs. Gunnery (Washington, CT) | | - |
| Sat 5/26 @ 2:00 PM | Varsity Baseball Game | vs. Kent School (Kent, CT)* | | - |