| Thu | 10/1/2026 4:00:00 PM | Freshman Football v St Johns Shrewsbury | Masco Football Field |
| Thu - NEW DATE | 10/1/2026 4:00:00 PM | Varsity Boys Soccer v Beverly | Masco Varsity Soccer Field Streaming Link |
| Fri | 10/2/2026 4:00:00 PM | Freshman Boys Soccer @ Peabody | Peabody HS |
| Fri | 10/2/2026 4:00:00 PM | Freshman Girls Soccer v TBD | Masco Freshman Soccer Field |
| Fri | 10/2/2026 4:00:00 PM | Varsity Field Hockey v Beverly | Boxford Common Turf Field |
| Fri | 10/2/2026 5:30:00 PM | JV Field Hockey v Beverly | Boxford Common Turf Field |
| Fri | 10/2/2026 6:00:00 PM | Varsity Football @ St Johns Shrewsbury | Shrewsbury, Pioneer Field |
| Sat | 10/3/2026 10:00:00 AM | JV Football v St Johns Shrewsbury | Masco Football Field |
| Sat | 10/3/2026 10:00:00 AM | JV Girls Soccer v North Andover | Masco JV Soccer Field |
| Sat | 10/3/2026 10:00:00 AM | Varsity Girls Soccer v North Andover | Masco Varsity Soccer Field |
| Sun | 10/4/2026 9:30:00 AM | Congregational Church of Topsfield - Worship Service | Comcast Ch 8 / Verizon Ch 45 |
| Sun | 10/4/2026 12:00:00 PM | October Fun Fest | West Boxford Gazebo |
| Mon | 10/5/2026 4:00:00 PM | Freshman Girls Soccer v Marblehead | Masco Freshman Soccer Field |
| Mon | 10/5/2026 4:00:00 PM | Freshman Volleyball @ Marblehead | Marblehead HS |
| Mon | 10/5/2026 4:00:00 PM | JV Volleyball @ Marblehead | Marblehead HS |
| Mon - Senior Night | 10/5/2026 4:00:00 PM | Varsity Boys Soccer v Saugus | Masco Varsity Soccer Field Streaming Link |
| Mon | 10/5/2026 4:30:00 PM | JV Boys Soccer v Saugus | Masco JV Soccer Field |
| Mon | 10/5/2026 4:30:00 PM | JV Girls Soccer @ Saugus | Saugus Anna Parker Playground |
| Mon - New Date | 10/5/2026 4:30:00 PM | Varsity Field Hockey v Swampscott | Boxford Common Turf Field |
| Mon | 10/5/2026 4:30:00 PM | Varsity Girls Soccer @ Saugus | Saugus HS |
| Mon | 10/5/2026 5:30:00 PM | Varsity Volleyball @ Marblehead | Marblehead HS |
| Tue | 10/6/2026 4:00:00 PM | Freshman Boys Soccer @ Marblehead | Marblehead Village Hopkins |
| Tue | 10/6/2026 4:00:00 PM | Varsity Field Hockey @ Danvers | Danvers HS |
| Wed | 10/7/2026 4:00:00 PM | Cross Country v Beverly | Bradley Palmer State Park |
| Wed | 10/7/2026 4:00:00 PM | Freshman Boys Soccer v TBD | Masco Freshman Soccer Field |
| Wed | 10/7/2026 4:00:00 PM | Freshman Volleyball @ Salem | Salem HS |
| Wed | 10/7/2026 4:00:00 PM | JV Boys Soccer v Marblehead | Masco JV Soccer Field |
| Wed | 10/7/2026 4:00:00 PM | JV Girls Soccer @ Marblehead | Marblehead Village Hopkins |
| Wed | 10/7/2026 4:00:00 PM | JV Volleyball @ Salem | Salem HS |
| Wed | 10/7/2026 4:00:00 PM | Varsity Boys Soccer v Marblehead | Masco Varsity Soccer Field Streaming Link |
| Wed | 10/7/2026 4:00:00 PM | Varsity Girls Soccer @ Marblehead | Marblehead HS |
| Wed | 10/7/2026 5:00:00 PM | Varsity Volleyball @ Salem | Salem HS |
| 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 |
| 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 |
| 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 |