| Sport | Date | Teams | Location | Time |
| Boys Soccer | Oct 26 | Gateway at McCann Tech | | 04:00 PM |
| Boys Soccer | Oct 26 | P.V.C.S. at Drury | | 04:00 PM |
| Boys Soccer | Oct 26 | Athol at Hoosac Valley | | 04:00 PM |
| Boys Soccer | Oct 26 | S. Hadley at Pittsfield | Kirvin Park | 04:15 PM |
| co-ed Volleyball | Oct 26 | Athol at Lee | Class D WMass quarter-final | 06:00 PM |
| co-ed Volleyball | Oct 26 | Commerce at Monument Mountain | Class B WMass quarter-final | 06:00 PM |
| co-ed Volleyball | Oct 26 | Lenox at Ware | Class D WMass quarter-final | 06:00 PM |
| co-ed Volleyball | Oct 26 | Wahconah at Chicopee | Class B WMass quarter-final | 06:00 PM |
| co-ed Volleyball | Oct 26 | Mount Everett at Mount Greylock | Class D WMass quarter-final | 06:00 PM |
| co-ed Volleyball | Oct 26 | Taconic at Southwick | Class C WMass quarter-final | 06:00 PM |
| Girls Soccer | Oct 26 | Chicopee Comp at Pittsfield | Kirvin Park | 02:30 PM |
| Girls Soccer | Oct 26 | Southwick at Lee | | 04:00 PM |
| |
| Boys Basketball | Oct 27 | Mount Greylock at Wahconah | Unified Basketball | 05:30 PM |
| Boys Soccer | Oct 27 | Lenox at Springfield ICS | Class C WMass semi-final | 03:30 PM |
| Boys Soccer | Oct 27 | Mount Everett at Ware | Class D WMass semi-final | 03:30 PM |
| Boys Soccer | Oct 27 | Mount Greylock at Pathfinder | Class C WMass semi-final | 03:30 PM |
| Boys Soccer | Oct 27 | Pope Francis at Wahconah | Time TBA | 12:00 AM |
| Boys Soccer | Oct 27 | Monument Mountain at Hampshire | Class B WMass semi-final Time TBA | 12:00 PM |
| co-ed Volleyball | Oct 27 | Pittsfield at W. Springfield | | 06:00 PM |
| Girls Soccer | Oct 27 | Smith Vocational at McCann Tech | | 03:30 PM |
| Girls Soccer | Oct 27 | Mount Everett at Lenox | Class D WMass semi-final | 03:30 PM |
| Girls Soccer | Oct 27 | Drury at Mount Greylock | Class C WMass semi-final | 06:30 PM |
| Girls Soccer | Oct 27 | Easthampton at Monument Mountain | Time TBA | 12:00 AM |
| Girls Soccer | Oct 27 | Pope Francis at Wahconah | Time TBA | 12:00 AM |
| Girls Soccer | Oct 27 | Hoosac Valley at Ware | Time TBA | 12:00 AM |
| |
| Boys Soccer | Oct 28 | McCann Tech at Taconic | BCC | 04:00 PM |
| Boys Soccer | Oct 28 | Pittsfield at Minnechaug | | 04:00 PM |
| Boys Soccer | Oct 28 | Hoosac Valley at Mohawk | | 04:00 PM |
| Football | Oct 28 | Hoosac Valley at Commerce | | 06:00 PM |
| Girls Soccer | Oct 28 | Pittsfield at Mahar | | 04:00 PM |
| Girls Soccer | Oct 28 | Lee at Holyoke | | 04:00 PM |
| Girls Soccer | Oct 28 | Pioneer Valley Chinese Immersion at Taconic | | 04:15 PM |
| |
| Boys Soccer | Oct 29 | Taconic at Gateway | | 04:00 PM |
| Boys Soccer | Oct 29 | Drury at Putnam | | 04:00 PM |
| Football | Oct 29 | S. Hadley at Taconic | | 06:00 PM |
| Football | Oct 29 | Lee at Belchertown | | 07:00 PM |
| Football | Oct 29 | Pittsfield at Ludlow | | 07:00 PM |
| Football | Oct 29 | W. Springfield at Wahconah | | 07:00 PM |
| Girls Soccer | Oct 29 | Taconic at Pathfinder | | 04:00 PM |
| |
| co-ed Cross Country | Oct 30 | Multiple teams at Berkshire County Invitational | Mount Greylock | 11:00 AM |
| Football | Oct 30 | Smith Vocational at McCann Tech | | 01:00 PM |
| Football | Oct 30 | Monument Mountain at Drury | | 01:00 PM |
| |
| co-ed Golf | Nov 02 | Multiple teams at Division 3 State Championship | Shining Rock, Northbridge | 10:00 AM |
| |
| Boys Basketball | Nov 08 | Pittsfield at Mount Greylock | Unified Basketball | 06:00 PM |
| |
| 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 |
| |
| 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 |
