SCHEDULE
| Sport | Date | Teams | Location | Time |
| Football | Oct 25 | Pittsfield at Taconic | 04:30 PM | |
| Football | Oct 25 | Smith Vocational at Monument Mountain | 06:00 PM | |
| Football | Oct 25 | Wahconah at Northampton | 07:00 PM | |
| Football | Oct 25 | Hoosac Valley at Lee | 07:00 PM | |
| Football | Oct 25 | McCann Tech at Pathfinder | 07:00 PM | |
| Football | Oct 26 | Springfield ICS at Drury | 11:55 AM | |
| Volleyball | Oct 26 | Lenox at Mount Greylock | Taconic, WMass Class C Final | 01:00 PM |
| Volleyball | Oct 26 | Wahconah at Baystate Academy | Chicopee Comp, WMass Class B Final | 10:00 AM |
| Volleyball | Oct 26 | Turners Falls at Lee | West Springfield, WMass Class D Final | 10:00 AM |
| Boys Basketball | Oct 28 | Wahconah at Lenox Unified | 04:30 PM | |
| Boys Basketball | Oct 29 | Pittsfield at Westfield Unified | 03:30 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 | |
| Football | Nov 01 | Drury at McCann Tech | 07:00 PM | |
| Football | Nov 01 | E. Longmeadow at Wahconah | 07:00 PM | |
| Football | Nov 01 | Frontier at Lee | 07:00 PM | |
| Football | Nov 01 | Ludlow at Taconic | 07:00 PM | |
| Football | Nov 02 | Putnam Voc at Pittsfield | 07:00 PM | |
| Football | Nov 02 | Easthampton at Hoosac Valley | 11:55 AM | |
| Boys Basketball | Nov 06 | Mount Greylock at Pittsfield Unified | 04:00 PM | |
| Boys Basketball | Nov 06 | Frontier Unified at Wahconah | 04:30 PM | |
| Boys Basketball | Nov 06 | Lenox at Monument Mountain Unified | 04:30 PM | |
| co-ed Cross Country | Nov 09 | Multiple teams at D3 all-state qualifier | Wrentham Development Center | 11:00 AM |
| co-ed Cross Country | Nov 16 | Multiple teams at D3 State Championships | Fort Devens | 02:00 PM |
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