| Sport | Date | Teams | Location | Time |
| Girls Soccer | Oct 15 | Mount Greylock at Lee | | 04:30 PM |
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| Boys Basketball | Oct 17 | Mount Greylock at Wahconah | Unified Basketball | 04:30 PM |
| Boys Soccer | Oct 17 | Monument Mountain at Mount Greylock | | 04:00 PM |
| Girls Soccer | Oct 17 | Mount Greylock at Monument Mountain | | 06:00 PM |
| |
| Boys Soccer | Oct 21 | Mount Greylock at Wahconah | | 04:30 PM |
| Girls Soccer | Oct 21 | Wahconah at Mount Greylock | | 06:30 PM |
| |
| Boys Soccer | Oct 23 | West Springfield at Mount Greylock | | 06:30 PM |
| Girls Soccer | Oct 23 | Mount Greylock at Mount Everett | | 04:15 PM |
| |
| Boys Basketball | Oct 24 | Mount Greylock at Northampton | Unified Basketball | 05:00 PM |
| |
| Boys Soccer | Oct 25 | Mount Greylock at Lenox | | 06:00 PM |
| |
| Boys Soccer | Oct 28 | Frontier at Mount Greylock | | 06:30 PM |
| Girls Soccer | Oct 28 | Mount Greylock at Hoosac Valley | | 04:30 PM |
| |
| Boys Basketball | Oct 29 | Wahconah at Mount Greylock | Unified Basketball | 06:00 PM |
| |
| Boys Soccer | Oct 30 | Mount Greylock at Minnechaug | | 05:00 PM |
| Girls Soccer | Oct 30 | Mahar at Mount Greylock | | 04:00 PM |
