| Wed 5/2 @ 3:00 PM | Varsity Baseball Game | vs. Deerfield Academy (Deerfield, MA)* | | - |
| Wed 5/2 @ 3:00 PM | Varsity Girls Lacrosse Game | vs. Wilbraham & Monson Academy (Wilbraham, MA)* | | - |
| Wed 5/2 @ 3:30 PM | Varsity Lacrosse Game | @ Proctor Academy (Andover, NH) | | - |
| Fri 5/4 @ 4:00 PM | Varsity Lacrosse Game | vs. Lawrence Academy (Groton, MA) | | - |
| Fri 5/4 @ 5:00 PM | Varsity Baseball Game | vs. Northfield Mount Hermon (Mount Hermon, MA)* | | - |
| Sat 5/5 @ 3:30 PM | Varsity Lacrosse Game | vs. Wilbraham & Monson Academy (Wilbraham, MA)* | | - |
| Sat 5/5 @ 4:00 PM | Varsity Baseball Game | @ Northfield Mount Hermon (Mount Hermon, MA)* | | - |
| Sat 5/5 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Kimball Union Academy (Meriden, NH)* | | - |
| Sat 5/5 @ 4:00 PM | JV Girls Lacrosse Game | @ Kimball Union Academy (Meriden, NH) | | - |
| Wed 5/9 @ 3:00 PM | Varsity Baseball Game | @ Phillips Academy (Andover, MA)* | | - |
| Wed 5/9 @ 3:00 PM | Varsity Softball Game | @ Northfield Mount Hermon (Mount Hermon, MA) | | - |
| Wed 5/9 @ 3:30 PM | JV Baseball Game | vs. Worcester Academy (Worcester, MA) | | - |
| Wed 5/9 @ 4:00 PM | JV Baseball Game | vs. Worcester Academy (Worcester, MA) | | - |
| Wed 5/9 @ 4:30 PM | Varsity Girls Lacrosse Game | @ Winchendon (MA) | | - |
| Fri 5/11 @ 4:15 PM | Varsity Baseball Game | @ Belmont Hill (Belmont, MA) | | - |
| Fri 5/11 @ 4:30 PM | JV Lacrosse Game | vs. Pingree (South Hamilton, MA) | | - |
| Fri 5/11 @ 4:30 PM | Varsity Lacrosse Game | vs. Pingree (South Hamilton, MA)* | | - |
| Fri 5/11 @ 5:00 PM | JV Baseball Game | @ Northfield Mount Hermon (Mount Hermon, MA) | | - |
| Sat 5/12 @ 12:00 PM | Varsity Girls Lacrosse Game | vs. Lawrence Academy (Groton, MA)* | | - |
| Sat 5/12 @ 2:30 PM | Varsity Baseball Game | @ Phillips Exeter Academy (Exeter, NH)* | | - |
| Wed 5/16 @ 3:30 PM | Varsity Baseball Game | @ Worcester Academy (Worcester, MA)* | | - |
| Wed 5/16 @ 4:00 PM | Varsity Lacrosse Game | vs. Worcester Academy (Worcester, MA)* | | - |
| Wed 5/16 @ 4:00 PM | JV Lacrosse Game | vs. Worcester Academy (Worcester, MA) | | - |
| Sat 5/19 @ TBA | Varsity Baseball Game | @ Phillips Academy (Andover, MA)* | | - |