| Sport | Date | Teams | Location | Time |
| Boys Soccer | Oct 23 | Frontier at Wahconah | | 01:00 PM |
| co-ed Volleyball | Oct 23 | Lee at Lenox | | 11:30 AM |
| Football | Oct 23 | Lee at Hoosac Valley | | 01:30 PM |
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| Girls Soccer | Oct 24 | Mount Everett at Berkshire Country Day | Time TBA | 12:00 PM |
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| co-ed Golf | Oct 25 | Multiple teams at Division 2 State Championship | Sandy Burr Country Club, Wayland | 09:00 AM |
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| co-ed Golf | Oct 26 | Multiple teams at Division 3 State Championship | Shining Rock, Northbridge | 10:00 AM |
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| Boys Basketball | Oct 27 | Mount Greylock at Wahconah | Unified Basketball | 05:30 PM |
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| Football | Oct 28 | Hoosac Valley at Commerce | | 06:00 PM |
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| Football | Oct 29 | S. Hadley at Taconic | | 06:00 PM |
| Football | Oct 29 | Pittsfield at Ludlow | | 07:00 PM |
| Football | Oct 29 | W. Springfield at Wahconah | | 07:00 PM |
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| co-ed Cross Country | Oct 30 | Multiple teams at Berkshire County Invitational | Mount Greylock | 11:00 AM |
| Football | Oct 30 | Monument Mountain at Drury | | 01:00 PM |
| Football | Oct 30 | Smith Vocational at McCann Tech | | 01:00 PM |
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| Boys Basketball | Nov 08 | Pittsfield at Mount Greylock | Unified Basketball | 06:00 PM |
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| co-ed Cross Country | Nov 13 | Multiple teams at D3 all-state qualifier | Stanley Park, Westfield | 10:00 AM |
| co-ed Cross Country | Nov 13 | Pittsfield at D2 all-state qualifier | Gardner Golf Course | 11:30 AM |
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| co-ed Cross Country | Nov 20 | Multiple teams at D3 State Championships | Wrentham Development Center | 01:00 PM |
| co-ed Cross Country | Nov 20 | TBA at D2 State Championships | Wrentham Development Center | 11:30 AM |
