| Fri | 9/25/2026 4:00:00 PM | Freshman Boys Soccer v Hamilton Wenham | Masco Freshman Soccer Field |
| Fri | 9/25/2026 4:00:00 PM | Freshman Girls Soccer @ Hamilton | Hamilton Donovan |
| Fri | 9/25/2026 4:00:00 PM | JV Boys Soccer @ Manchester-Essex | Manchester-Essex HS |
| Fri | 9/25/2026 4:00:00 PM | Varsity Boys Soccer @ Manchester | Manchester HS |
| Fri | 9/25/2026 4:30:00 PM | Varsity Field Hockey v Swampscott | Boxford Common Turf Field |
| Fri | 9/25/2026 6:00:00 PM | JV Field Hockey v Swampscott | Boxford Common Turf Field |
| Fri | 9/25/2026 6:30:00 PM | Varsity Football v Winchester | Masco Football Field |
| Sat | 9/26/2026 1:23:00 AM | Cross Country @ TBD | Wrentham Development Center |
| Sat | 9/26/2026 9:30:00 AM | JV Football @ Winchester | Winchester, Ciarcia Field |
| Sat | 9/26/2026 11:00:00 AM | Varsity Girls Soccer @ Bishop Feehan | Bishop Feehan HS |
| Sun | 9/27/2026 9:30:00 AM | Congregational Church of Topsfield - Worship Service | Comcast Ch 8 / Verizon Ch 45 |
| Mon | 9/28/2026 4:00:00 PM | JV Boys Soccer v Beverly | Masco JV Soccer Field |
| Mon | 9/28/2026 4:00:00 PM | JV Girls Soccer @ Beverly | Beverly HS |
| Mon | 9/28/2026 4:00:00 PM | Varsity Boys Soccer v Beverly | Masco Varsity Soccer Field |
| Mon | 9/28/2026 4:00:00 PM | Varsity Girls Soccer @ Beverly | Beverly HS |
| Mon | 9/28/2026 4:30:00 PM | Freshman Girls Soccer v North Reading | Masco Freshman Soccer Field |
| Mon | 9/28/2026 4:30:00 PM | JV Volleyball @ Winthrop | Winthrop HS |
| Mon | 9/28/2026 4:45:00 PM | Freshman Boys Soccer @ North Reading | North Reading HS |
| Mon | 9/28/2026 5:45:00 PM | Varsity Volleyball @ Winthrop | Winthrop HS |
| Tue | 9/29/2026 4:00:00 PM | Varsity Field Hockey v Pentucket | Boxford Common Turf Field |
| Tue | 9/29/2026 5:30:00 PM | JV Field Hockey v Pentucket | Boxford Common Turf Field |
| Wed | 9/30/2026 4:00:00 PM | Cross Country @ Swampscott | Swampscott, Upper Jackson Field |
| Wed | 9/30/2026 4:00:00 PM | Freshman Boys Soccer @ Newburyport | Newburyport HS |
| Wed | 9/30/2026 4:00:00 PM | Freshman Girls Soccer v Newburyport | Masco Freshman Soccer Field |
| Wed | 9/30/2026 4:00:00 PM | Freshman Volleyball v Danvers | Masco Field House |
| Wed | 9/30/2026 4:00:00 PM | JV Boys Soccer v Peabody | Masco JV Soccer Field |
| Wed | 9/30/2026 4:00:00 PM | JV Girls Soccer @ Peabody | Peabody HS |
| Wed | 9/30/2026 4:00:00 PM | JV Volleyball v Danvers | Masco Gym |
| Wed | 9/30/2026 4:00:00 PM | Varsity Boys Soccer v Peabody | Masco Varsity Soccer Field |
| Wed | 9/30/2026 4:00:00 PM | Varsity Girls Soccer @ Peabody | Peabody HS |
| Wed | 9/30/2026 5:30:00 PM | Varsity Volleyball v Danvers | Masco Gym |
| Thu | 10/1/2026 4:00:00 PM | Freshman Football v St Johns Shrewsbury | Masco Football Field |
| 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 | 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 |
| 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 |