| Sport | Date | Teams | Location | Time |
| Girls Soccer | Oct 15 | Hoosac Valley at Taconic | BCC | 07:30 PM |
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| Boys Soccer | Oct 16 | Lenox at Hoosac Valley | | 04:30 PM |
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| Girls Soccer | Oct 17 | Hoosac Valley at Pittsfield | | 04:30 PM |
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| Football | Oct 18 | Chicopee at Hoosac Valley | Renfrew | 07:00 PM |
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| Boys Soccer | Oct 19 | Taconic at Hoosac Valley | | 10:00 AM |
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| Girls Soccer | Oct 21 | Monument Mountain at Hoosac Valley | | 04:30 PM |
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| Boys Soccer | Oct 22 | Mount Everett at Hoosac Valley | | 04:00 PM |
| Girls Soccer | Oct 22 | Hoosac Valley at Mount Everett | | 04:30 PM |
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| Girls Soccer | Oct 23 | Hoosac Valley at Lenox | | 06:00 PM |
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| Boys Soccer | Oct 25 | Taconic at Hoosac Valley | | 04:00 PM |
| Football | Oct 25 | Ludlow at Hoosac Valley | Renfrew | 07:00 PM |
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| Girls Soccer | Oct 28 | Mount Greylock at Hoosac Valley | | 04:30 PM |
