| Sport | Date | Teams | Location | Time |
| Boys Soccer | Oct 18 | McCann Tech at P.V.C.S. | | 04:00 PM |
| Boys Soccer | Oct 18 | Mount Everett at Lenox | | 06:00 PM |
| Boys Soccer | Oct 18 | Wahconah at Pittsfield | BCC | 06:30 PM |
| co-ed Golf | Oct 18 | Multiple teams at Western Mass D2 Meet | Berkshire Hills, Pittsfield | 10:00 AM |
| co-ed Volleyball | Oct 18 | Mount Everett at Science and Technology | | 05:00 PM |
| co-ed Volleyball | Oct 18 | Mount Greylock at Easthampton | | 06:00 PM |
| co-ed Volleyball | Oct 18 | Chicopee at Lenox | | 06:00 PM |
| co-ed Volleyball | Oct 18 | Pittsfield at Agawam | | 06:00 PM |
| co-ed Volleyball | Oct 18 | Monument Mountain at Science and Technology | | 06:00 PM |
| co-ed Volleyball | Oct 18 | Wahconah at Pioneer Valley | | 06:00 PM |
| co-ed Volleyball | Oct 18 | West Springfield at Lee | | 06:00 PM |
| Girls Soccer | Oct 18 | Pioneer Valley at Drury | | 04:00 PM |
| Girls Soccer | Oct 18 | Mount Everett at Hopkins | | 04:30 PM |
| Girls Soccer | Oct 18 | Pittsfield at Agawam | | 04:30 PM |
| Girls Soccer | Oct 18 | Mount Greylock at Hoosac Valley | Renfrew | 06:30 PM |
| Girls Soccer | Oct 18 | Wahconah at Hampshire | | 06:30 PM |
| |
| Boys Soccer | Oct 19 | McCann Tech at Taconic | | 04:00 PM |
| Boys Soccer | Oct 19 | Westfield Tech at Hoosac Valley | | 04:30 PM |
| Boys Soccer | Oct 19 | Drury at Putnam | | 06:00 PM |
| Boys Soccer | Oct 19 | Agawam at Mount Greylock | | 06:30 PM |
| Boys Soccer | Oct 19 | Monument Mountain at Westfield | | 07:00 PM |
| Boys Soccer | Oct 19 | Lenox at Wahconah | | 07:00 PM |
| co-ed Cross Country | Oct 19 | Pope Francis at McCann Tech | Greylock Glen | 04:00 PM |
| co-ed Golf | Oct 19 | Multiple teams at Western Mass D3 Meet | Country Club of Greenfield | 09:00 AM |
| co-ed Volleyball | Oct 19 | Mount Everett at Taconic | | 06:00 PM |
| Girls Soccer | Oct 19 | Taconic at Drury | | 04:00 PM |
| Girls Soccer | Oct 19 | Monument Mountain at Granby | | 04:00 PM |
| Girls Soccer | Oct 19 | Hampden Charter School of Science at Lee | | 04:30 PM |
| Girls Soccer | Oct 19 | Lenox at Chicopee | | 06:00 PM |
| |
| Boys Soccer | Oct 20 | Pittsfield at Pope Francis | | 04:30 PM |
| co-ed Cross Country | Oct 20 | Multiple teams at Pittsfield | | 04:00 PM |
| co-ed Cross Country | Oct 20 | Multiple teams at Hoosac Valley | | 04:30 PM |
| co-ed Volleyball | Oct 20 | Taconic at Holyoke | | 05:00 PM |
| co-ed Volleyball | Oct 20 | Wahconah at Mahar | | 05:00 PM |
| co-ed Volleyball | Oct 20 | Lenox at Easthampton | | 05:00 PM |
| co-ed Volleyball | Oct 20 | Putnam at Mount Everett | | 06:00 PM |
| co-ed Volleyball | Oct 20 | E. Longmeadow at Mount Greylock | | 06:00 PM |
| co-ed Volleyball | Oct 20 | Pittsfield at S. Hadley | | 06:00 PM |
| co-ed Volleyball | Oct 20 | Monument Mountain at Springfield Central | | 06:00 PM |
| Girls Soccer | Oct 20 | Mount Greylock at Lee | | 04:30 PM |
| Girls Soccer | Oct 20 | McCann Tech at Wahconah | | 06:00 PM |
| |
| Boys Soccer | Oct 21 | Lenox at Monument Mountain | | 07:00 PM |
| Boys Soccer | Oct 21 | McCann Tech at Hoosac Valley | Renfrew | 07:00 PM |
| co-ed Volleyball | Oct 21 | Lee at Lenox | | 06:00 PM |
| Girls Soccer | Oct 21 | Monument Mountain at Pittsfield | | 04:00 PM |
| Girls Soccer | Oct 21 | Mount Everett at Berkshire Country Day | | 04:00 PM |
| Girls Soccer | Oct 21 | Ware at Hoosac Valley | Renfrew | 05:00 PM |
| |
| Boys Soccer | Oct 22 | Ludlow at Mount Greylock | | 04:30 PM |
| Boys Soccer | Oct 22 | Mahar at Wahconah | | 07:00 PM |
| co-ed Volleyball | Oct 22 | Pittsfield at Ludlow | | 06:00 PM |
| co-ed Volleyball | Oct 22 | Agawam at Lee | | 06:00 PM |
| co-ed Volleyball | Oct 22 | Mount Greylock at Wahconah | | 06:00 PM |
| Football | Oct 22 | Pittsfield at Taconic | | 06:00 PM |
| Football | Oct 22 | Drury at Smith Vocational | | 06:00 PM |
| Football | Oct 22 | Monument Mountain at Pathfinder | | 07:00 PM |
| Football | Oct 22 | Northampton at Wahconah | | 07:30 PM |
| Girls Soccer | Oct 22 | Mount Greylock at Lenox | | 06:30 PM |
| |
| Boys Soccer | Oct 23 | Frontier at Wahconah | | 01:00 PM |
| Football | Oct 23 | Lee at Hoosac Valley | | 01:30 PM |
| |
| Girls Soccer | Oct 24 | Mount Everett at Berkshire Country Day | Time TBA | 12:00 PM |
| |
| Football | Oct 28 | Hoosac Valley at Commerce | | 06:00 PM |
| |
| Football | Oct 29 | S. Hadley at Taconic | | 06:00 PM |
| Football | Oct 29 | Pittsfield at Ludlow | | 07:00 PM |
| Football | Oct 29 | W. Springfield at Wahconah | | 07:00 PM |
| |
| co-ed Cross Country | Oct 30 | Multiple teams at Berkshire County Invitational | Mount Greylock | 11:00 AM |
| Football | Oct 30 | Monument Mountain at Drury | | 01:00 PM |
| Football | Oct 30 | Smith Vocational at McCann Tech | | 01:00 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 |
