| Thu | 10/8/2026 4:00:00 PM | Freshman Football v Peabody | Masco Football Field |
| Fri | 10/9/2026 4:00:00 PM | JV Boys Soccer v Mystic Valley | Masco JV Soccer Field |
| Fri | 10/9/2026 4:00:00 PM | Varsity Boys Soccer v Mystic Valley | Masco Varsity Soccer Field Streaming Link |
| Fri | 10/9/2026 4:00:00 PM | Varsity Field Hockey v Peabody` | Boxford Common Turf Field |
| Fri | 10/9/2026 5:30:00 PM | JV Field Hockey v Peabody | Boxford Common Turf Field |
| Fri | 10/9/2026 7:00:00 PM | Varsity Football @ Peabody | Peabody HS |
| Sat | 10/10/2026 10:00:00 AM | JV Football v Peabody | Masco Football Field |
| Wed | 10/14/2026 4:00:00 PM | Cross Country v Salem | Bradley Palmer State Park |
| Wed | 10/14/2026 4:00:00 PM | Freshman Boys Soccer v Beverly | Masco Freshman Soccer Field |
| Wed | 10/14/2026 4:00:00 PM | Freshman Girls Soccer @ Lynnfield | Lynnfield HS |
| Wed | 10/14/2026 4:00:00 PM | Freshman Volleyball v Beverly | Masco Field House |
| Wed | 10/14/2026 4:00:00 PM | JV Volleyball v Beverly | Masco Gym |
| Wed | 10/14/2026 4:00:00 PM | Varsity Field Hockey v Malden Catholic | Boxford Common Turf Field |
| Wed | 10/14/2026 5:30:00 PM | Varsity Volleyball v Beverly | Masco Gym |
| Thu | 10/15/2026 4:00:00 PM | Freshman Football @ Danvers | Danvers HS |
| Thu | 10/15/2026 4:00:00 PM | JV Boys Soccer @ Marblehead | Marblehead Village Hopkins |
| Thu | 10/15/2026 4:00:00 PM | Varsity Boys Soccer @ Marblehead | Marblehead HS Streaming Link |
| Fri | 10/16/2026 1:23:00 AM | Cross Country @ TBD | Cape Cod Fairgrounds |
| Fri | 10/16/2026 4:00:00 PM | Freshman Boys Soccer @ Hamilton | Hamilton Donovan |
| Fri | 10/16/2026 4:00:00 PM | Freshman Girls Soccer v Hamilton-Wenham | Masco Freshman Soccer Field |
| Fri | 10/16/2026 4:00:00 PM | JV Boys Soccer @ Fenwick | Bishop Fenwick HS |
| Fri | 10/16/2026 4:00:00 PM | JV Volleyball @ Essex Tech | Essex Tech |
| Fri | 10/16/2026 4:00:00 PM | Varsity Boys Soccer @ Bishop Fenwick | Bishop Fenwick |
| Fri | 10/16/2026 4:30:00 PM | Varsity Field Hockey v Gloucester | Boxford Common Turf Field |
| Fri | 10/16/2026 5:00:00 PM | Varsity Volleyball @ Essex Tech | Essex Tech |
| Fri | 10/16/2026 6:00:00 PM | JV Field Hockey v Gloucester | Boxford Common Turf Field |
| Fri | 10/16/2026 6:30:00 PM | Varsity Football v Danvers | Masco Football Field |
| Sat | 10/17/2026 9:00:00 AM | JV Football @ Danvers | Danvers HS |
| Sat | 10/17/2026 12:00:00 PM | JV Girls Soccer @ Central Catholic | Central Catholic HS |
| Sat | 10/17/2026 2:00:00 PM | Varsity Girls Soccer @ Central Catholic | Central Catholic HS |
| Mon | 10/19/2026 4:00:00 PM | Freshman Volleyball @ Peabody | Peabody HS |
| Mon | 10/19/2026 4:00:00 PM | JV Boys Soccer v Swampscott | Masco JV Soccer Field |
| Mon | 10/19/2026 4:00:00 PM | JV Volleyball @ Peabody | Peabody HS |
| Mon | 10/19/2026 4:00:00 PM | Varsity Boys Soccer v Swampscott | Masco Varsity Soccer Field Streaming Link |
| Mon | 10/19/2026 4:00:00 PM | Varsity Field Hockey v Marblehead | Boxford Common Turf Field |
| Mon | 10/19/2026 4:30:00 PM | JV Girls Soccer @ Swampscott | Swampscott Upper Jackson Field |
| Mon | 10/19/2026 4:30:00 PM | Varsity Girls Soccer @ Swampscott | Swampscott Phillips Blocksidge |
| Mon | 10/19/2026 4:45:00 PM | Freshman Boys Soccer v North Reading | Masco Freshman Soccer Field |
| Mon | 10/19/2026 4:45:00 PM | Freshman Girls Soccer @ North Reading | North Reading HS |
| Mon | 10/19/2026 5:30:00 PM | JV Field Hockey v Marblehead | Boxford Common Turf Field |
| Mon | 10/19/2026 5:30:00 PM | Varsity Volleyball @ Peabody | Peabody HS |
| Wed | 10/21/2026 4:00:00 PM | Cross Country v Danvers | Bradley Palmer State Park |
| Wed | 10/21/2026 4:00:00 PM | JV Boys Soccer v Danvers | Masco JV Soccer Field |
| Wed | 10/21/2026 4:00:00 PM | JV Girls Soccer @ Danvers | Danvers HS |
| Wed | 10/21/2026 4:00:00 PM | JV Volleyball @ Hamilton-Wenham | Hamilton-Wenham HS |
| Wed | 10/21/2026 4:00:00 PM | Varsity Boys Soccer v Danvers | Masco Varsity Soccer Field Streaming Link |
| Wed | 10/21/2026 5:00:00 PM | Varsity Volleyball @ Hamilton-Wenham | Hamilton-Wenham HS |
| Wed | 10/21/2026 6:30:00 PM | Varsity Girls Soccer @ Danvers | Danvers HS |
| Thu | 10/22/2026 4:00:00 PM | Freshman Football v Beverly | Masco Football Field |
| Thu | 10/22/2026 4:00:00 PM | JV Volleyball v Ipswich | Masco Gym |
| Thu | 10/22/2026 4:30:00 PM | Freshman Boys Soccer @ North Andover | North Andover HS |
| Thu | 10/22/2026 4:30:00 PM | Freshman Girls Soccer @ North Andover | North Andover HS |
| Thu | 10/22/2026 5:30:00 PM | Varsity Volleyball v Ipswich | Masco Gym |
| Fri | 10/23/2026 4:00:00 PM | JV Girls Soccer v Andover | Masco JV Soccer Field |
| Fri | 10/23/2026 4:00:00 PM | Varsity Girls Soccer v Andover | Masco Varsity Soccer Field Streaming Link |
| Fri | 10/23/2026 4:30:00 PM | JV Field Hockey @ Beverly | Beverly HS |
| Fri | 10/23/2026 6:00:00 PM | Varsity Field Hockey @ Beverly | Beverly Turf Field |