| Wed | 9/9/2026 4:00:00 PM | Cross Country @ Saugus | Deer Island |
| Wed | 9/9/2026 4:00:00 PM | Freshman Boys Soccer v Newburyport | Masco Freshman Soccer Field |
| Wed | 9/9/2026 4:00:00 PM | Freshman Girls Soccer @ Newburyport | Newburyport HS |
| Wed | 9/9/2026 4:00:00 PM | Freshman Volleyball v Marblehead | Masco Field House |
| Wed | 9/9/2026 4:00:00 PM | JV Volleyball v Marblehead | Masco Gym |
| Wed | 9/9/2026 5:30:00 PM | Varsity Volleyball v Marblehead | Masco Gym |
| Wed | 9/9/2026 7:00:00 PM | Boxford Board of Health | 7A Spofford Rd, Mtg Room 1 Streaming Link |
| Thu | 9/10/2026 4:00:00 PM | JV Girls Soccer v Marblehead | Masco JV Soccer Field |
| Thu | 9/10/2026 4:00:00 PM | Varsity Field Hockey @ Peabody | Peabody HS |
| Thu | 9/10/2026 4:00:00 PM | Varsity Girls Soccer v Marblehead | Masco Varsity Soccer Field |
| Fri | 9/11/2026 4:00:00 PM | Freshman Boys Soccer v Peabody | Masco Freshman Soccer Field |
| Fri | 9/11/2026 4:00:00 PM | JV Volleyball @ Pentucket | Pentucket HS |
| Fri | 9/11/2026 5:15:00 PM | Varsity Volleyball @ Pentucket | Pentucket HS |
| Fri | 9/11/2026 6:30:00 PM | Varsity Football v Billerica | Masco Football Field |
| Sat | 9/12/2026 9:00:00 AM | Freshman Football @ Biullerica | Billerica HS |
| Sat | 9/12/2026 10:30:00 AM | Cross Country @ TBA | Newburyport, Maudsley State Park |
| Sat | 9/12/2026 10:30:00 AM | Cross Country @ TBD | Newburyport, Maudsley State Park |
| Sun | 9/13/2026 10:00:00 AM | Home Run Derby | Jim Locke Field - Boy Scout Park |
| Sun | 9/13/2026 1:00:00 PM | MSB Annual All Star Game | Jim Locke Field - Boy Scout Park |
| Mon | 9/14/2026 4:00:00 PM | Freshman Volleyball @ Beverly | Beverly HS |
| Mon | 9/14/2026 4:00:00 PM | JV Boys Soccer v Gloucester | Masco JV Soccer Field |
| Mon | 9/14/2026 4:00:00 PM | JV Volleyball @ Beverly | Beverly HS |
| Mon | 9/14/2026 4:00:00 PM | Varsity Boys Soccer v Gloucester | Masco Varsity Soccer Field |
| Mon | 9/14/2026 4:30:00 PM | JV Girls Soccer @ Gloucester | O'Maley/Talbot Rink Hockey |
| Mon | 9/14/2026 4:30:00 PM | Varsity Girls Soccer @ Gloucester | Gloucester HS |
| Mon | 9/14/2026 5:00:00 PM | JV Football @ Billerica | Billerica HS |
| Tue | 9/15/2026 4:30:00 PM | Varsity Field Hockey @ Saugus | Saugus HS |
| Tue | 9/15/2026 5:30:00 PM | JV Field Hockey @ Marblehead | Marblehead HS |
| Tue | 9/15/2026 6:00:00 PM | JV Field Hockey @ Saugus | Saugus HS |
| Wed | 9/16/2026 4:00:00 PM | Cross Country v Marblehead | Bradley Palmer State Park |
| Wed | 9/16/2026 4:00:00 PM | Freshman Boys Soccer v Marblehead | Masco Freshman Soccer Field |
| Wed | 9/16/2026 4:30:00 PM | Freshman Volleyball v Saugus | Masco Field House |
| Wed | 9/16/2026 4:30:00 PM | JV Volleyball v Saugus | Masco Gym |
| Wed | 9/16/2026 6:00:00 PM | Varsity Volleyball v Saugus | Masco Gym |
| Thu | 9/17/2026 4:00:00 PM | Freshman Girls Soccer @ Marblehead | Marblehead Village Hopkins |
| Thu | 9/17/2026 4:00:00 PM | Varsity Field Hockey @ Marblehead | Marblehead HS |
| Thu | 9/17/2026 4:15:00 PM | JV Girls Soccer v Winchester | Masco JV Soccer Field |
| Thu | 9/17/2026 4:15:00 PM | Varsity Girls Soccer v Winchester | Masco Varsity Soccer Field |
| Fri | 9/18/2026 4:00:00 PM | Freshman Boys Soccer @ TBD | Essex Tech |
| Fri | 9/18/2026 4:00:00 PM | JV Boys Soccer v Whittier | Masco JV Soccer Field |
| Fri | 9/18/2026 4:00:00 PM | Varsity Boys Soccer v Whitter HS | Masco Varsity Soccer Field |
| Fri | 9/18/2026 6:30:00 PM | Varsity Football v North Andover | Masco Football Field |
| Sat | 9/19/2026 9:00:00 AM | Freshman Football @ North Andover | North Andover HS |
| Sat | 9/19/2026 10:00:00 AM | Concert: Apple Festival | Boxford Melvin Green |
| Sat | 9/19/2026 10:45:00 AM | JV Football @ North Andover | North Andover HS |
| Mon | 9/21/2026 4:00:00 PM | Freshman Boys Soccer @ Beverly | Beverly HS |
| Mon | 9/21/2026 4:00:00 PM | Freshman Girls Soccer v Lynnfield | Masco Freshman Soccer Field |
| Mon | 9/21/2026 4:00:00 PM | Freshman Volleyball v Newburyport | Masco Field House |
| Mon | 9/21/2026 4:00:00 PM | JV Boys Soccer @ Danvers | Danvers HS |
| Mon | 9/21/2026 4:00:00 PM | JV Girls Soccer v Danvers | Masco JV Soccer Field |
| Mon | 9/21/2026 4:00:00 PM | JV Volleyball v Newburyport | Masco Gym |
| Mon | 9/21/2026 4:00:00 PM | Varsity Boys Soccer @ Danvers | Danvers HS |
| Mon | 9/21/2026 4:00:00 PM | Varsity Field Hockey @ Manchester-Essex | Manchester-Essex HS |
| Mon | 9/21/2026 4:00:00 PM | Varsity Girls Soccer v Danvers | Masco Varsity Soccer Field |
| Mon | 9/21/2026 5:15:00 PM | JV Field Hockey @ Manchester-Essex | Manchester-Essex HS |
| Mon | 9/21/2026 5:30:00 PM | Varsity Volleyball v Newburyport | Masco Gym |
| Wed | 9/23/2026 4:00:00 PM | Cross Country @ Peabody | Peabody HS |
| Wed | 9/23/2026 4:00:00 PM | Freshman Volleyball v Peabody | Masco Field House |
| Wed | 9/23/2026 4:00:00 PM | JV Girls Soccer v Winthrop | Masco JV Soccer Field |
| Wed | 9/23/2026 4:00:00 PM | JV Volleyball v Peabody | Masco Gym |
| Wed | 9/23/2026 4:30:00 PM | JV Boys Soccer @ Winthrop | Winthrop HS |
| Wed | 9/23/2026 4:30:00 PM | Varsity Boys Soccer @ Winthrop | Winthrop HS |
| Wed | 9/23/2026 5:30:00 PM | Varsity Volleyball v Peabody | Masco Gym |
| Wed | 9/23/2026 6:00:00 PM | Varsity Girls Soccer v Winthrop | Masco Football Field |
| Thu | 9/24/2026 4:00:00 PM | Freshman Boys Soccer v North Andover | Masco Freshman Soccer Field |
| Thu | 9/24/2026 4:30:00 PM | Freshman Girls Soccer v North Andover | Masco Freshman Soccer Field |