| Wed 5/2 @ TBA | Varsity Lacrosse Game | vs. Lawrenceville School (Lawrenceville, NJ) | | - |
| Wed 5/2 @ 3:00 PM | Varsity Baseball Game | @ Cushing Academy (Ashburnham, MA)* | | - |
| Sat 5/5 @ TBA | Varsity Lacrosse Game | vs. Hotchkiss (Lakeville, CT)* | | - |
| Sat 5/5 @ 3:30 PM | Varsity Baseball Game | vs. Worcester Academy (Worcester, MA)* | | - |
| Wed 5/9 @ TBA | Varsity Lacrosse Game | @ Kent School (Kent, CT)* | | - |
| Wed 5/9 @ 2:30 PM | Varsity Baseball Game | @ Northfield Mount Hermon (Mount Hermon, MA)* | | - |
| Sat 5/12 @ TBA | Varsity Lacrosse Game | @ Avon Old Farms (Avon, CT)* | | - |
| Sat 5/12 @ 1:00 PM | Varsity Baseball Game | @ Phillips Academy (Andover, MA)* | | - |
| Sat 5/12 @ 3:00 PM | Varsity Baseball Game | @ Phillips Academy (Andover, MA)* | | - |
| Mon 5/14 @ 4:30 PM | Varsity Baseball Game | @ Williston Northampton (Easthampton, MA) | | - |
| Wed 5/16 @ TBA | Varsity Lacrosse Game | vs. Salisbury School (Salisbury, CT)* | | - |
| Wed 5/16 @ 3:00 PM | Varsity Baseball Game | vs. Avon Old Farms (Avon, CT) | | - |
| Sat 5/19 @ TBA | Varsity Lacrosse Game | @ Phillips Academy (Andover, MA) | | - |
| Sat 5/19 @ TBA | Varsity Baseball Game | @ Choate Rosemary Hall (Wallingford, CT)** | | - |
| Sat 5/19 @ 12:30 PM | Varsity Baseball Game | @ Northfield Mount Hermon (Mount Hermon, MA)** | | - |