SCHEDULE
| Sport | Date | Teams | Location | Time |
| Boys Soccer | Oct 07 | Pope Francis at Monument Mountain | 04:30 PM | |
| Girls Soccer | Oct 08 | Mount Greylock at Monument Mountain | 06:00 PM | |
| Boys Soccer | Oct 09 | Monument Mountain at Mount Greylock | 06:30 PM | |
| Volleyball | Oct 10 | Monument Mountain at Taconic | 06:00 PM | |
| Football | Oct 11 | Pathfinder at Monument Mountain | 07:00 PM | |
| Girls Soccer | Oct 11 | Hoosac Valley at Monument Mountain | 04:30 PM | |
| Girls Soccer | Oct 14 | Monument Mountain at Housatonic Regional | 04:00 PM | |
| Volleyball | Oct 14 | Monument Mountain at Lee | 06:00 PM | |
| Boys Soccer | Oct 16 | Westfield at Monument Mountain | 04:00 PM | |
| Girls Soccer | Oct 16 | Monument Mountain at Wahconah | 07:00 PM | |
| Volleyball | Oct 17 | Veritas Prep Charter at Monument Mountain | 05:30 PM | |
| Football | Oct 18 | Monument Mountain at McCann Tech | 07:00 PM | |
| Boys Soccer | Oct 19 | Ludlow at Monument Mountain | 06:00 PM | |
| Boys Soccer | Oct 21 | Monument Mountain at Westfield | 04:00 PM | |
| Girls Soccer | Oct 21 | S. Hadley at Monument Mountain | 06:00 PM | |
| Boys Basketball | Oct 22 | Southwick Unified at Monument Mountain | 04:30 PM | |
| Girls Soccer | Oct 23 | Chicopee at Monument Mountain | 04:00 PM | |
| Football | Oct 25 | Smith Vocational at Monument Mountain | 06:00 PM | |
| Boys Basketball | Oct 29 | Monument Mountain at Mount Greylock Unified | 05:30 PM | |
| Football | Nov 01 | Monument Mountain at Springfield ICS | 06:00 PM | |
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Stringer Scores Game-Winner as Wahconah Tops Lenox
