| Sport | Date | Teams | Location | Time |
| Boys Soccer | Oct 15 | Sabis at Mount Everett | | 04:00 PM |
| Boys Soccer | Oct 15 | Monument Mountain at Mahar | | 04:00 PM |
| Boys Soccer | Oct 15 | McCann Tech at Smith Voc. | | 04:00 PM |
| Boys Soccer | Oct 15 | Wahconah at Pittsfield | Kirvin Park | 04:15 PM |
| Boys Soccer | Oct 15 | Smith Academy at Taconic | BCC | 04:30 PM |
| co-ed Cross Country | Oct 15 | Multiple teams at McCann Tech | | 04:00 PM |
| co-ed Golf | Oct 15 | McCann Tech at Monson | | 03:00 PM |
| co-ed Golf | Oct 15 | Monument Mountain at Hoosac Valley | | 03:30 PM |
| co-ed Golf | Oct 15 | Lenox at Wahconah | | 03:30 PM |
| co-ed Golf | Oct 15 | Lee at Mount Greylock | | 03:30 PM |
| co-ed Volleyball | Oct 15 | Pittsfield at Mt. Anthony (VT) | | 05:45 PM |
| co-ed Volleyball | Oct 15 | Mount Everett at Wahconah | | 06:15 PM |
| Girls Soccer | Oct 15 | Mount Greylock at Lee | | 04:30 PM |
| Girls Soccer | Oct 15 | Drury at Lenox | | 06:00 PM |
| Girls Soccer | Oct 15 | Monument Mountain at Wahconah | | 06:30 PM |
| Girls Soccer | Oct 15 | Hoosac Valley at Taconic | BCC | 07:30 PM |
| |
| Boys Soccer | Oct 16 | Wahconah at Drury | | 04:00 PM |
| Boys Soccer | Oct 16 | Lenox at Hoosac Valley | | 04:30 PM |
| co-ed Cross Country | Oct 16 | Pittsfield at Mount Greylock | | 04:30 PM |
| co-ed Cross Country | Oct 16 | Wahconah at Mount Everett | | 04:30 PM |
| co-ed Cross Country | Oct 16 | Monument Mountain at Mount Everett | | 04:30 PM |
| co-ed Cross Country | Oct 16 | Lenox at Mount Greylock | | 04:30 PM |
| co-ed Cross Country | Oct 16 | Taconic at Mount Everett | | 04:30 PM |
| co-ed Volleyball | Oct 16 | Mount Everett at Lenox | | 05:45 PM |
| co-ed Volleyball | Oct 16 | Pittsfield at Taconic | | 06:00 PM |
| co-ed Volleyball | Oct 16 | Mount Greylock at Lee | | 06:00 PM |
| Girls Soccer | Oct 16 | McCann Tech at Westfield Tech | | 04:00 PM |
| |
| Boys Soccer | Oct 17 | Monument Mountain at Mount Greylock | | 04:00 PM |
| Boys Soccer | Oct 17 | Putnam at McCann Tech | | 04:00 PM |
| Boys Soccer | Oct 17 | Taconic at Drury | | 04:30 PM |
| Girls Soccer | Oct 17 | Hoosac Valley at Pittsfield | | 04:30 PM |
| Girls Soccer | Oct 17 | Mount Greylock at Monument Mountain | | 06:00 PM |
| Girls Soccer | Oct 17 | Lenox at Wahconah | | 06:00 PM |
| |
| Boys Soccer | Oct 18 | Wahconah at Mount Everett | | 04:00 PM |
| Boys Soccer | Oct 18 | Pittsfield at Lenox | | 06:00 PM |
| co-ed Volleyball | Oct 18 | Mount Everett at Housatonic Valley RHS | | 05:15 PM |
| co-ed Volleyball | Oct 18 | Mount Greylock at Pittsfield | | 05:45 PM |
| co-ed Volleyball | Oct 18 | Lee at Mt. Anthony (VT) | | 05:45 PM |
| co-ed Volleyball | Oct 18 | Taconic at Monument Mountain | | 06:00 PM |
| Football | Oct 18 | E. Longmeadow at Wahconah | | 07:00 PM |
| Football | Oct 18 | Athol at Drury | Mount Greylock | 07:00 PM |
| Football | Oct 18 | Taconic at Putnam | Central High | 07:00 PM |
| Football | Oct 18 | Pittsfield at Amherst | | 07:00 PM |
| Football | Oct 18 | Belchertown at Lee | | 07:00 PM |
| Football | Oct 18 | Chicopee at Hoosac Valley | Renfrew | 07:00 PM |
| Football | Oct 18 | Easthampton at Monument Mountain | | 07:00 PM |
| Girls Soccer | Oct 18 | St Mary’s at McCann Tech | | 04:00 PM |
| Girls Soccer | Oct 18 | Pittsfield at Drury | | 04:00 PM |
| Girls Soccer | Oct 18 | Mount Everett at Lenox | | 04:00 PM |
| |
| Boys Soccer | Oct 19 | Pittsfield at Southwick | | 02:00 PM |
| Boys Soccer | Oct 19 | Taconic at Hoosac Valley | | 10:00 AM |
| Boys Soccer | Oct 19 | Mount Everett at Berkshire Country Day Tournament | Time TBA | 12:00 PM |
| co-ed Volleyball | Oct 19 | Pittsfield at Southwick | | 09:30 AM |
| Football | Oct 19 | Smith Vocational at McCann Tech | | 01:00 PM |
| |
| Boys Soccer | Oct 21 | Mohawk at McCann Tech | | 04:00 PM |
| Boys Soccer | Oct 21 | Mount Greylock at Wahconah | | 04:30 PM |
| Boys Soccer | Oct 21 | Pittsfield at Ludlow | | 04:30 PM |
| Boys Soccer | Oct 21 | Lenox at Monument Mountain | | 06:00 PM |
| co-ed Golf | Oct 21 | Multiple teams at Western Mass D3 Meet | Agawam Municipal | 09:00 AM |
| co-ed Golf | Oct 21 | Multiple teams at Western Mass D1 Meet | Southampton Country Club | 09:00 AM |
| co-ed Volleyball | Oct 21 | Taconic at Mount Everett | | 06:00 PM |
| co-ed Volleyball | Oct 21 | Lenox at Wahconah | | 06:30 PM |
| Girls Soccer | Oct 21 | Lee at Drury | | 04:00 PM |
| Girls Soccer | Oct 21 | Monument Mountain at Hoosac Valley | | 04:30 PM |
| Girls Soccer | Oct 21 | Taconic at Mount Everett | | 04:30 PM |
| Girls Soccer | Oct 21 | Wahconah at Mount Greylock | | 06:30 PM |
| |
| Boys Soccer | Oct 22 | Drury at Taconic | BCC | 04:00 PM |
| Boys Soccer | Oct 22 | Mount Everett at Hoosac Valley | | 04:00 PM |
| co-ed Cross Country | Oct 22 | McCann Tech at Frontier | | 04:00 PM |
| co-ed Golf | Oct 22 | Multiple teams at Western Mass D2 Meet | Country Club of Pittsfield | 09:00 AM |
| co-ed Volleyball | Oct 22 | S. Hadley at Taconic | | 06:00 PM |
| co-ed Volleyball | Oct 22 | Pittsfield at Tantasqua | | 06:00 PM |
| co-ed Volleyball | Oct 22 | Lee at Frontier | Time TBA | 12:00 PM |
| Girls Soccer | Oct 22 | Commerce at McCann Tech | | 04:00 PM |
| Girls Soccer | Oct 22 | Pittsfield at Springfield Central | | 04:00 PM |
| Girls Soccer | Oct 22 | Hoosac Valley at Mount Everett | | 04:30 PM |
| |
| Boys Soccer | Oct 23 | Mount Everett at Wahconah | | 06:00 PM |
| Boys Soccer | Oct 23 | West Springfield at Mount Greylock | | 06:30 PM |
| co-ed Volleyball | Oct 23 | Lenox at Pittsfield | | 06:00 PM |
| co-ed Volleyball | Oct 23 | Mount Greylock at Mount Everett | | 06:00 PM |
| Girls Soccer | Oct 23 | Lee at Greenfield High School | | 04:00 PM |
| Girls Soccer | Oct 23 | Mount Greylock at Mount Everett | | 04:15 PM |
| Girls Soccer | Oct 23 | Hoosac Valley at Lenox | | 06:00 PM |
| |
| Boys Basketball | Oct 24 | Mount Greylock at Northampton | Unified Basketball | 05:00 PM |
| Boys Soccer | Oct 24 | McCann Tech at P.V.C.S. | | 04:00 PM |
| co-ed Volleyball | Oct 24 | Lenox at Mount Greylock | | 05:45 PM |
| co-ed Volleyball | Oct 24 | Hampden Charter at Pittsfield | | 06:00 PM |
| co-ed Volleyball | Oct 24 | Lee at Taconic | | 06:00 PM |
| Girls Soccer | Oct 24 | Wahconah at West Springfield | | 07:00 PM |
| |
| Boys Soccer | Oct 25 | Taconic at Hoosac Valley | | 04:00 PM |
| Boys Soccer | Oct 25 | Mount Everett at Drury | | 04:00 PM |
| Boys Soccer | Oct 25 | Pittsfield at Monument Mountain | | 06:00 PM |
| Boys Soccer | Oct 25 | Mount Greylock at Lenox | | 06:00 PM |
| co-ed Volleyball | Oct 25 | Monument Mountain at Taconic | | 06:00 PM |
| co-ed Volleyball | Oct 25 | Mount Greylock at Wahconah | | 06:30 PM |
| Football | Oct 25 | Putnam at Pittsfield | BCC | 06:00 PM |
| Football | Oct 25 | Ludlow at Hoosac Valley | Renfrew | 07:00 PM |
| Football | Oct 25 | Drury at Ware | | 07:00 PM |
| Football | Oct 25 | Monument Mountain at Greenfield | | 07:00 PM |
| Football | Oct 25 | Wahconah at W. Springfield | | 07:00 PM |
| Football | Oct 25 | McCann Tech at Palmer | | 07:00 PM |
| Girls Soccer | Oct 25 | McCann Tech at Duggan | | 04:00 PM |
| Girls Soccer | Oct 25 | Lenox at Lee | | 04:00 PM |
| Girls Soccer | Oct 25 | Monument Mountain at Pittsfield | | 04:15 PM |
| Girls Soccer | Oct 25 | Drury at Taconic | Crosby | 04:30 PM |
| |
| co-ed Cross Country | Oct 26 | Multiple teams at Berkshire County Championship | Time TBA, Reid MS | 10:00 AM |
| co-ed Volleyball | Oct 26 | Wahconah at Monument Mountain | | 02:30 PM |
| Football | Oct 26 | E. Longmeadow at Taconic | BCC | 06:00 PM |
| Girls Soccer | Oct 26 | Wahconah at Lincoln-Sudbury | | 01:00 PM |
| |
| Boys Soccer | Oct 28 | Frontier at Mount Greylock | | 06:30 PM |
| co-ed Golf | Oct 28 | Multiple teams at Division 3 State Championship | Cranberry Valley Golf Course (Harwich) | 09:00 AM |
| co-ed Volleyball | Oct 28 | Duggan at Mount Everett | varsity only | 04:30 PM |
| co-ed Volleyball | Oct 28 | Lenox at Taconic | | 06:00 PM |
| co-ed Volleyball | Oct 28 | Mount Greylock at Wahconah | | 06:30 PM |
| Girls Soccer | Oct 28 | Hampden Charter School of Science at McCann Tech | | 04:00 PM |
| Girls Soccer | Oct 28 | Monument Mountain at Westfield | | 04:00 PM |
| Girls Soccer | Oct 28 | Mount Greylock at Hoosac Valley | | 04:30 PM |
| Girls Soccer | Oct 28 | Drury at Mount Everett | | 04:30 PM |
| Girls Soccer | Oct 28 | Taconic at Lenox | | 06:00 PM |
| |
| Boys Basketball | Oct 29 | Wahconah at Mount Greylock | Unified Basketball | 06:30 PM |
| Boys Soccer | Oct 29 | Lenox at Mount Everett | | 04:00 PM |
| Boys Soccer | Oct 29 | Monument Mountain at Belchertown | | 04:00 PM |
| Boys Soccer | Oct 29 | Pittsfield at Shepherd Hill | | 06:00 PM |
| co-ed Golf | Oct 29 | Multiple teams at Division 2 State Championship | Taconic Golf Club | 09:00 AM |
| Girls Soccer | Oct 29 | Wahconah at Pittsfield | BCC | 07:30 PM |
| |
| Boys Soccer | Oct 30 | Mohawk at Drury | | 04:00 PM |
| Boys Soccer | Oct 30 | Mount Greylock at Minnechaug | | 05:00 PM |
| Boys Soccer | Oct 30 | Athol at Wahconah | | 06:00 PM |
| Girls Soccer | Oct 30 | Mahar at Mount Greylock | | 04:00 PM |
| Girls Soccer | Oct 30 | Mount Everett at Lee | | 04:00 PM |
| Girls Soccer | Oct 30 | Drury at Monument Mountain | | 06:30 PM |
| |
| Football | Nov 01 | Pittsfield at Taconic | BCC | 06:30 PM |
| Football | Nov 01 | Turners Falls at Monument Mountain | | 07:00 PM |
| Football | Nov 01 | Minnechaug at Wahconah | | 07:00 PM |
| Football | Nov 01 | Lee at Ludlow | | 07:00 PM |
| |
| Football | Nov 02 | Mohawk at Drury | | 01:00 PM |
| Football | Nov 02 | Pathfinder at McCann Tech | | 01:00 PM |
| |
| co-ed Cross Country | Nov 09 | Multiple teams at Western Mass | TBA | 10:00 AM |
| |
| co-ed Cross Country | Nov 16 | Multiple teams at State Championships | Gardner Municipal Golf Course | 10:00 AM |
