| Sport | Date | Teams | Location | Time |
| co-ed Golf | Aug 29 | Mount Everett at Pittsfield | | 03:30 PM |
| co-ed Golf | Aug 29 | Taconic at Monument Mountain | | 03:30 PM |
| co-ed Golf | Aug 29 | Mount Greylock at Lenox | | 03:30 PM |
| co-ed Golf | Aug 29 | Monument Mountain at Wahconah | | 04:00 PM |
| |
| co-ed Golf | Aug 30 | Mount Greylock at Hoosac Valley | | 03:30 PM |
| |
| co-ed Golf | Sep 02 | Taconic at Pittsfield | | 03:30 PM |
| |
| Boys Soccer | Sep 03 | McCann Tech at St Mary’s | | 04:00 PM |
| Boys Soccer | Sep 03 | Mount Greylock at Longmeadow | | 06:30 PM |
| co-ed Golf | Sep 03 | Lenox at Taconic | | 03:30 PM |
| co-ed Golf | Sep 03 | Lee at Pittsfield | | 03:30 PM |
| co-ed Volleyball | Sep 03 | Pittsfield at Lenox | | 05:45 PM |
| Girls Soccer | Sep 03 | Taconic at Mount Greylock | | 04:30 PM |
| Girls Soccer | Sep 03 | Burr and Burton at Monument Mountain | | 04:30 PM |
| Girls Soccer | Sep 03 | Lenox at Pittsfield | BCC | 07:00 PM |
| |
| Boys Soccer | Sep 04 | Hoosac Valley at Monument Mountain | | 03:30 PM |
| Boys Soccer | Sep 04 | Taconic at Holyoke | | 04:00 PM |
| Boys Soccer | Sep 04 | Chicopee at Pittsfield | | 04:30 PM |
| co-ed Cross Country | Sep 04 | Taconic at Monument Mountain | | 04:30 PM |
| co-ed Cross Country | Sep 04 | Lenox at Monument Mountain | | 04:30 PM |
| co-ed Cross Country | Sep 04 | Mount Greylock at Monument Mountain | | 04:30 PM |
| co-ed Cross Country | Sep 04 | Pittsfield at Monument Mountain | | 04:30 PM |
| co-ed Cross Country | Sep 04 | Wahconah at Monument Mountain | | 04:30 PM |
| co-ed Golf | Sep 04 | Mt. Anthony (VT) at Pittsfield | | 03:30 PM |
| |
| co-ed Golf | Sep 05 | Taconic at Mount Greylock | | 03:30 PM |
| co-ed Golf | Sep 05 | Monument Mountain at Lenox | | 04:00 PM |
| co-ed Volleyball | Sep 05 | Mount Greylock at Monument Mountain | | 06:00 PM |
| co-ed Volleyball | Sep 05 | Chic Comp at Taconic | | 06:00 PM |
| Girls Soccer | Sep 05 | McCann Tech at Science and Technology | | 04:00 PM |
| Girls Soccer | Sep 05 | Pittsfield at Mount Greylock | | 04:30 PM |
| Girls Soccer | Sep 05 | Taconic at Lee | | 05:00 PM |
| |
| Boys Soccer | Sep 06 | Mount Everett at Taconic | BCC | 04:00 PM |
| Boys Soccer | Sep 06 | Commerce at McCann Tech | | 04:00 PM |
| Boys Soccer | Sep 06 | Drury at Hoosac Valley | | 04:00 PM |
| Boys Soccer | Sep 06 | Monument Mountain at Frontier | | 04:30 PM |
| Boys Soccer | Sep 06 | Mount Greylock at Pittsfield | BCC | 06:00 PM |
| co-ed Golf | Sep 06 | Taconic at Mt. Anthony (VT) | | 03:30 PM |
| co-ed Golf | Sep 06 | Taconic at Hoosac Valley | | 03:30 PM |
| Football | Sep 06 | Drury at Monument Mountain | | 07:00 PM |
| Football | Sep 06 | Taconic at Westfield | Bullens | 07:00 PM |
| |
| co-ed Volleyball | Sep 09 | Mount Everett at Mount Greylock | | 05:30 PM |
| co-ed Volleyball | Sep 09 | Wahconah at Taconic | | 06:00 PM |
| Girls Soccer | Sep 09 | Putnam at McCann Tech | | 04:00 PM |
| Girls Soccer | Sep 09 | Lenox at Taconic | BCC | 04:30 PM |
| Girls Soccer | Sep 09 | Pittsfield at Mount Everett | | 04:30 PM |
| Girls Soccer | Sep 09 | Monument Mountain at Ware | | 04:30 PM |
| |
| Boys Soccer | Sep 10 | Westfield Tech at McCann Tech | | 04:00 PM |
| Boys Soccer | Sep 10 | Mount Greylock at Monument Mountain | | 04:30 PM |
| Boys Soccer | Sep 10 | Taconic at Drury | | 04:30 PM |
| Boys Soccer | Sep 10 | Pittsfield at Wahconah | | 07:00 PM |
| co-ed Cross Country | Sep 10 | McCann Tech at Franklin Tech | | 04:00 PM |
| co-ed Golf | Sep 10 | Monument Mountain at Mount Greylock | | 03:30 PM |
| Girls Soccer | Sep 10 | Drury at Mahar | | 04:30 PM |
| |
| co-ed Cross Country | Sep 11 | Taconic at Mount Everett | | 04:30 PM |
| co-ed Cross Country | Sep 11 | Pittsfield at Wahconah | | 04:30 PM |
| co-ed Cross Country | Sep 11 | Monument Mountain at Mount Everett | | 04:30 PM |
| co-ed Cross Country | Sep 11 | Mount Greylock at Wahconah | | 04:30 PM |
| co-ed Golf | Sep 11 | Pittsfield at Lenox | | 03:30 PM |
| co-ed Volleyball | Sep 11 | Lee at Pittsfield | | 05:45 PM |
| co-ed Volleyball | Sep 11 | Wahconah at Mount Greylock | | 05:45 PM |
| Girls Soccer | Sep 11 | Pathfinder at McCann Tech | | 04:00 PM |
| Girls Soccer | Sep 11 | Monument Mountain at Mount Greylock | | 04:30 PM |
| Girls Soccer | Sep 11 | Pittsfield at Chicopee Comp | | 04:30 PM |
| Girls Soccer | Sep 11 | Drury at Lenox | | 07:00 PM |
| |
| Boys Soccer | Sep 12 | Franklin Tech at McCann Tech | | 04:00 PM |
| Boys Soccer | Sep 12 | Mohawk at Monument Mountain | | 04:30 PM |
| Boys Soccer | Sep 12 | Mahar at Taconic | BCC | 05:00 PM |
| Boys Soccer | Sep 12 | Drury at Wahconah | | 06:30 PM |
| co-ed Golf | Sep 12 | Mount Everett at Taconic | | 03:30 PM |
| co-ed Golf | Sep 12 | E. Longmeadow at Pittsfield | | 03:30 PM |
| co-ed Golf | Sep 12 | Mount Greylock at Mount Everett | | 03:30 PM |
| co-ed Golf | Sep 12 | Monument Mountain at Lee | | 04:00 PM |
| co-ed Volleyball | Sep 12 | Mount Everett at Taconic | | 06:00 PM |
| Girls Soccer | Sep 12 | Taconic at Easthampton | | 04:30 PM |
| |
| Boys Soccer | Sep 13 | Pittsfield at Minnechaug | | 04:00 PM |
| co-ed Golf | Sep 13 | Taconic at Wahconah | | 03:30 PM |
| co-ed Volleyball | Sep 13 | E. Longmeadow at Pittsfield | | 05:45 PM |
| co-ed Volleyball | Sep 13 | Ludlow at Taconic | | 06:00 PM |
| co-ed Volleyball | Sep 13 | Monument Mountain at Lenox | | 06:00 PM |
| Football | Sep 13 | Frontier at Monument Mountain | | 07:00 PM |
| Football | Sep 13 | McCann Tech at Mahar | | 07:00 PM |
| Football | Sep 13 | Pittsfield at Wahconah | | 07:00 PM |
| Girls Soccer | Sep 13 | Franklin Tech at McCann Tech | | 04:00 PM |
| Girls Soccer | Sep 13 | Hoosac Valley at Drury | | 04:00 PM |
| Girls Soccer | Sep 13 | Lenox at Mount Greylock | | 06:00 PM |
| |
| Boys Soccer | Sep 14 | Taconic at Lenox | | 11:00 AM |
| Girls Soccer | Sep 14 | Taconic at Pittsfield | | 01:00 PM |
| |
| Boys Soccer | Sep 16 | McCann Tech at Mohawk | | 04:00 PM |
| Boys Soccer | Sep 16 | Longmeadow at Pittsfield | | 04:30 PM |
| Boys Soccer | Sep 16 | Taconic at Wahconah | | 06:00 PM |
| co-ed Volleyball | Sep 16 | Mt. Anthony (VT) at Pittsfield | | 05:45 PM |
| co-ed Volleyball | Sep 16 | Taconic at Mount Greylock | | 05:45 PM |
| co-ed Volleyball | Sep 16 | Monument Mountain at Wahconah | | 06:30 PM |
| Girls Soccer | Sep 16 | Westfield Tech at McCann Tech | | 04:00 PM |
| |
| Boys Soccer | Sep 17 | McCann Tech at Putnam | | 04:00 PM |
| co-ed Cross Country | Sep 17 | Multiple teams at McCann Tech | Windsor Lake | 04:00 PM |
| co-ed Golf | Sep 17 | Lee at Taconic | | 03:30 PM |
| co-ed Golf | Sep 17 | Mount Greylock at Lee | | 03:30 PM |
| co-ed Golf | Sep 17 | Pittsfield at Monument Mountain | | 03:30 PM |
| co-ed Volleyball | Sep 17 | Pittsfield at Hampden Charter | | 05:45 PM |
| Girls Soccer | Sep 17 | Drury at Mount Greylock | | 04:00 PM |
| Girls Soccer | Sep 17 | W. Springfield at Pittsfield | | 04:30 PM |
| Girls Soccer | Sep 17 | Hoosac Valley at Monument Mountain | | 06:00 PM |
| Girls Soccer | Sep 17 | Taconic at Wahconah | | 07:00 PM |
| |
| Boys Soccer | Sep 18 | Monument Mountain at Taconic | BCC | 04:30 PM |
| Boys Soccer | Sep 18 | Drury at Mohawk | | 04:30 PM |
| Boys Soccer | Sep 18 | Shepherd Hill at Pittsfield | | 05:00 PM |
| co-ed Cross Country | Sep 18 | Monument Mountain at Lenox | | 04:30 PM |
| co-ed Cross Country | Sep 18 | Taconic at Lee | | 04:30 PM |
| co-ed Cross Country | Sep 18 | Pittsfield at Lenox | | 04:30 PM |
| co-ed Cross Country | Sep 18 | Hoosac Valley at Lee | | 04:30 PM |
| co-ed Golf | Sep 18 | Pittsfield at Taconic | | 03:30 PM |
| |
| Boys Soccer | Sep 19 | West Springfield at Mount Greylock | | 05:00 PM |
| co-ed Golf | Sep 19 | Mount Greylock at Pittsfield | | 03:30 PM |
| co-ed Golf | Sep 19 | Monument Mountain at Mount Everett | | 03:30 PM |
| co-ed Volleyball | Sep 19 | Pittsfield at Taconic | | 05:45 PM |
| Girls Soccer | Sep 19 | McCann Tech at St Mary’s | | 04:00 PM |
| Girls Soccer | Sep 19 | Drury at Lee | | 04:00 PM |
| Girls Soccer | Sep 19 | Mount Greylock at Wahconah | | 06:00 PM |
| Girls Soccer | Sep 19 | Mount Everett at Taconic | | 07:00 PM |
| |
| Boys Soccer | Sep 20 | Lenox at Pittsfield | | 04:00 PM |
| Boys Soccer | Sep 20 | Mount Everett at Drury | | 04:30 PM |
| Boys Soccer | Sep 20 | Wahconah at Monument Mountain | | 06:30 PM |
| co-ed Golf | Sep 20 | Taconic at E. Longmeadow | | 03:30 PM |
| co-ed Volleyball | Sep 20 | Taconic at Duggan | | 04:30 PM |
| co-ed Volleyball | Sep 20 | Wahconah at Pittsfield | | 05:45 PM |
| co-ed Volleyball | Sep 20 | Mount Greylock at Westfield | | 06:30 PM |
| Football | Sep 20 | Monument Mountain at Athol | | 06:00 PM |
| Football | Sep 20 | Wahconah at Taconic | BCC | 07:00 PM |
| Girls Soccer | Sep 20 | Belchertown at Monument Mountain | | 04:00 PM |
| |
| Football | Sep 21 | Palmer at Drury | | 01:00 PM |
| Football | Sep 21 | McCann Tech at Ware | | 07:00 PM |
| Football | Sep 21 | Northampton at Pittsfield | BCC | 07:00 PM |
| |
| co-ed Volleyball | Sep 23 | Longmeadow at Pittsfield | | 05:45 PM |
| co-ed Volleyball | Sep 23 | Lenox at Monument Mountain | | 06:00 PM |
| co-ed Volleyball | Sep 23 | Amherst at Taconic | | 06:00 PM |
| co-ed Volleyball | Sep 23 | Mount Greylock at Wahconah | | 06:30 PM |
| Girls Soccer | Sep 23 | Mt. Anthony (VT) at Drury | | 04:00 PM |
| Girls Soccer | Sep 23 | Mount Everett at Mount Greylock | | 04:00 PM |
| Girls Soccer | Sep 23 | Pittsfield at Monument Mountain | | 06:00 PM |
| |
| Boys Soccer | Sep 24 | Pathfinder at McCann Tech | | 04:00 PM |
| Boys Soccer | Sep 24 | Hoosac Valley at Drury | | 04:00 PM |
| Boys Soccer | Sep 24 | Taconic at Mount Everett | | 04:30 PM |
| Boys Soccer | Sep 24 | Wahconah at Mount Greylock | | 04:30 PM |
| Boys Soccer | Sep 24 | Monument Mountain at Lenox | | 07:00 PM |
| co-ed Cross Country | Sep 24 | McCann Tech at Hampden Charter | | 04:00 PM |
| co-ed Golf | Sep 24 | Wahconah at Taconic | | 03:30 PM |
| co-ed Golf | Sep 24 | Mount Greylock at Monument Mountain | | 03:30 PM |
| Girls Soccer | Sep 24 | McCann Tech at Commerce | | 04:00 PM |
| |
| Boys Soccer | Sep 25 | Hoosac Valley at McCann Tech | | 04:00 PM |
| co-ed Cross Country | Sep 25 | Monument Mountain at Pittsfield | Reid MS | 04:30 PM |
| co-ed Cross Country | Sep 25 | Hoosac Valley at Pittsfield | Reid MS | 04:30 PM |
| co-ed Cross Country | Sep 25 | Taconic at Pittsfield | Reid MS | 04:30 PM |
| co-ed Cross Country | Sep 25 | Lee at Pittsfield | Reid MS | 04:30 PM |
| co-ed Golf | Sep 25 | Hoosac Valley at Mount Greylock | | 03:30 PM |
| co-ed Volleyball | Sep 25 | Pittsfield at Mount Greylock | | 05:45 PM |
| co-ed Volleyball | Sep 25 | Monument Mountain at Taconic | | 06:00 PM |
| Girls Soccer | Sep 25 | Mount Greylock at Drury | | 04:00 PM |
| Girls Soccer | Sep 25 | Monument Mountain at Taconic | | 04:30 PM |
| Girls Soccer | Sep 25 | Hoosac Valley at Pittsfield | | 04:30 PM |
| |
| Boys Soccer | Sep 26 | Monument Mountain at Pittsfield | | 04:30 PM |
| Boys Soccer | Sep 26 | Lenox at Mount Greylock | | 04:30 PM |
| Boys Soccer | Sep 26 | Drury at Taconic | BCC | 07:00 PM |
| co-ed Golf | Sep 26 | Lenox at Mount Greylock | | 03:30 PM |
| co-ed Golf | Sep 26 | Monument Mountain at Taconic | | 03:30 PM |
| co-ed Golf | Sep 26 | Pittsfield at Mount Everett | | 03:30 PM |
| Girls Soccer | Sep 26 | Duggan at McCann Tech | | 04:30 PM |
| |
| Boys Soccer | Sep 27 | P.V.C.S. at McCann Tech | | 04:00 PM |
| co-ed Volleyball | Sep 27 | Monument Mountain at Pittsfield | | 05:45 PM |
| co-ed Volleyball | Sep 27 | Lee at Mount Greylock | | 05:45 PM |
| Football | Sep 27 | Pittsfield at Lee | | 07:00 PM |
| Football | Sep 27 | Taconic at Commerce | Central High | 07:00 PM |
| Football | Sep 27 | Monument Mountain at Franklin Tech | | 07:00 PM |
| Girls Soccer | Sep 27 | McCann Tech at Taconic | Crosby | 04:00 PM |
| Girls Soccer | Sep 27 | Lenox at Monument Mountain | | 06:00 PM |
| Girls Soccer | Sep 27 | Drury at Wahconah | | 07:00 PM |
| |
| Boys Soccer | Sep 28 | Taconic at Athol | | 03:30 PM |
| Boys Soccer | Sep 28 | Pittsfield at W. Springfield | | 07:00 PM |
| Football | Sep 28 | Drury at McCann Tech | | 01:00 PM |
| |
| Girls Soccer | Sep 30 | McCann Tech at Hampden Charter School of Science | | 04:00 PM |
| |
| Boys Soccer | Oct 01 | McCann Tech at Duggan | | 04:00 PM |
| Boys Soccer | Oct 01 | Drury at Mount Everett | | 04:30 PM |
| co-ed Cross Country | Oct 01 | McCann Tech at Hopkins | | 04:00 PM |
| co-ed Golf | Oct 01 | Pittsfield at Lee | | 03:30 PM |
| co-ed Golf | Oct 01 | Lenox at Monument Mountain | | 03:30 PM |
| co-ed Golf | Oct 01 | Taconic at Lenox | | 03:30 PM |
| co-ed Volleyball | Oct 01 | Pittsfield at Mount Everett | | 05:45 PM |
| co-ed Volleyball | Oct 01 | Taconic at Lenox | | 06:00 PM |
| Girls Soccer | Oct 01 | Mount Everett at Drury | | 04:00 PM |
| |
| Boys Soccer | Oct 02 | Mount Everett at Monument Mountain | | 04:00 PM |
| Boys Soccer | Oct 02 | Mount Greylock at Easthampton | | 04:30 PM |
| Boys Soccer | Oct 02 | Lenox at Drury | | 04:30 PM |
| co-ed Cross Country | Oct 02 | Taconic at Mount Greylock | | 04:30 PM |
| co-ed Cross Country | Oct 02 | Mount Everett at Pittsfield | Reid MS | 04:30 PM |
| co-ed Cross Country | Oct 02 | Monument Mountain at Mount Greylock | | 04:30 PM |
| co-ed Cross Country | Oct 02 | Lenox at Pittsfield | Reid MS | 04:30 PM |
| co-ed Golf | Oct 02 | Hoosac Valley at Taconic | | 03:30 PM |
| co-ed Golf | Oct 02 | Pittsfield at Wahconah | | 03:30 PM |
| co-ed Volleyball | Oct 02 | Taconic at Pittsfield | | 05:45 PM |
| co-ed Volleyball | Oct 02 | Mount Greylock at Mt. Anthony (VT) | | 05:45 PM |
| Girls Soccer | Oct 02 | Science and Technology at McCann Tech | | 04:00 PM |
| Girls Soccer | Oct 02 | Hoosac Valley at Mount Greylock | | 04:15 PM |
| |
| Boys Soccer | Oct 03 | McCann Tech at Commerce | | 04:00 PM |
| co-ed Golf | Oct 03 | Mount Greylock at Taconic | | 03:30 PM |
| Girls Soccer | Oct 03 | Monument Mountain at Lee | | 04:30 PM |
| Girls Soccer | Oct 03 | Wahconah at Pittsfield | BCC | 07:00 PM |
| |
| Boys Soccer | Oct 04 | Monument Mountain at Hopkins | | 04:00 PM |
| Boys Soccer | Oct 04 | Wahconah at Taconic | Crosby | 04:30 PM |
| Boys Soccer | Oct 04 | Pittsfield at Mount Greylock | | 07:00 PM |
| Boys Soccer | Oct 04 | McCann Tech at Hoosac Valley | Renfrew | 07:00 PM |
| co-ed Golf | Oct 04 | Hoosac Valley at Pittsfield | | 03:30 PM |
| co-ed Volleyball | Oct 04 | Pittsfield at Lee | | 05:45 PM |
| co-ed Volleyball | Oct 04 | Mount Greylock at Lenox | | 06:00 PM |
| co-ed Volleyball | Oct 04 | Mt. Anthony (VT) at Taconic | | 06:00 PM |
| co-ed Volleyball | Oct 04 | Mount Everett at Monument Mountain | | 06:00 PM |
| Football | Oct 04 | S. Hadley at Pittsfield | BCC | 07:00 PM |
| Girls Soccer | Oct 04 | McCann Tech at Putnam | | 04:00 PM |
| Girls Soccer | Oct 04 | Taconic at Drury | | 04:30 PM |
| Girls Soccer | Oct 04 | Mount Greylock at Lenox | | 06:00 PM |
| |
| Boys Soccer | Oct 05 | Hoosac Valley at Pittsfield | | 01:00 PM |
| Football | Oct 05 | McCann Tech at Mohawk | | 01:00 PM |
| Football | Oct 05 | Drury at Pathfinder | | 01:00 PM |
| Football | Oct 05 | Amherst at Taconic | BCC | 06:00 PM |
| |
| Boys Soccer | Oct 07 | McCann Tech at Westfield Tech | | 04:00 PM |
| Boys Soccer | Oct 07 | Monument Mountain at Mount Greylock | | 04:00 PM |
| Boys Soccer | Oct 07 | Taconic at Hoosac Valley | | 04:30 PM |
| Boys Soccer | Oct 07 | Wahconah at Pittsfield | BCC | 06:30 PM |
| Boys Soccer | Oct 07 | Hoosac Valley at Taconic | BCC | 07:00 PM |
| co-ed Volleyball | Oct 07 | Mount Greylock at Taconic | | 05:45 PM |
| co-ed Volleyball | Oct 07 | Pittsfield at Wahconah | | 06:30 PM |
| Girls Soccer | Oct 07 | Mount Greylock at Pittsfield | Kirvin Park | 04:30 PM |
| |
| co-ed Cross Country | Oct 08 | Multiple teams at McCann Tech | | 04:00 PM |
| co-ed Golf | Oct 08 | Mount Everett at Monument Mountain | | 03:30 PM |
| Girls Soccer | Oct 08 | McCann Tech at Pathfinder | | 04:00 PM |
| Girls Soccer | Oct 08 | Lee at Taconic | | 05:15 PM |
| Girls Soccer | Oct 08 | Monument Mountain at Lenox | | 06:00 PM |
| |
| co-ed Golf | Oct 09 | Lenox at Pittsfield | | 03:30 PM |
| co-ed Golf | Oct 09 | Taconic at Mount Everett | | 03:30 PM |
| Football | Oct 09 | E. Longmeadow at Taconic | BCC | 06:00 PM |
| Girls Soccer | Oct 09 | Drury at Hoosac Valley | | 04:00 PM |
| |
| Boys Soccer | Oct 10 | Hampden Charter at McCann Tech | | 04:00 PM |
| Boys Soccer | Oct 10 | Drury at Hoosac Valley | | 04:00 PM |
| Boys Soccer | Oct 10 | Mount Everett at Taconic | BCC | 05:30 PM |
| co-ed Cross Country | Oct 10 | Mount Greylock at Hoosac Valley | | 04:30 PM |
| co-ed Cross Country | Oct 10 | Wahconah at Hoosac Valley | | 04:30 PM |
| co-ed Cross Country | Oct 10 | Taconic at Lenox | | 04:30 PM |
| co-ed Cross Country | Oct 10 | Mount Everett at Lenox | | 04:30 PM |
| co-ed Cross Country | Oct 10 | Monument Mountain at Lenox | | 04:30 PM |
| co-ed Cross Country | Oct 10 | Pittsfield at Hoosac Valley | | 04:30 PM |
| co-ed Golf | Oct 10 | Mount Everett at Mount Greylock | | 03:30 PM |
| co-ed Golf | Oct 10 | Lee at Monument Mountain | | 03:30 PM |
| co-ed Volleyball | Oct 10 | Monument Mountain at Lee | | 06:00 PM |
| co-ed Volleyball | Oct 10 | Taconic at Wahconah | | 06:30 PM |
| Girls Soccer | Oct 10 | Hoosac Valley at Pittsfield | | 04:00 PM |
| |
| Boys Soccer | Oct 11 | Wahconah at Drury | | 04:00 PM |
| Boys Soccer | Oct 11 | Ludlow at Mount Greylock | | 06:00 PM |
| Boys Soccer | Oct 11 | Monument Mountain at Wahconah | | 07:00 PM |
| co-ed Golf | Oct 11 | Taconic at Lee | | 03:30 PM |
| co-ed Volleyball | Oct 11 | Mt. Anthony (VT) at Mount Greylock | | 05:45 PM |
| Football | Oct 11 | Monument Mountain at Mahar | | 07:00 PM |
| Football | Oct 11 | W. Springfield at Pittsfield | BCC | 07:00 PM |
| Football | Oct 11 | Taconic at S. Hadley | | 07:00 PM |
| Girls Soccer | Oct 11 | Pittsfield at Belchertown | | 04:00 PM |
| Girls Soccer | Oct 11 | Drury at Mount Everett | | 04:30 PM |
| Girls Soccer | Oct 11 | Mount Greylock at Taconic | Crosby | 04:30 PM |
| Girls Soccer | Oct 11 | Wahconah at Monument Mountain | | 06:00 PM |
| |
| Boys Soccer | Oct 12 | Pittsfield at Taconic | BCC | 11:00 AM |
| co-ed Cross Country | Oct 12 | Taconic at Brown University Inv. | Time TBA | 10:00 AM |
| co-ed Volleyball | Oct 12 | Taconic at Pioneer Valley | | 11:30 AM |
| Football | Oct 12 | Smith Vocational at Drury | | 01:00 PM |
| |
| Boys Golf | Oct 13 | Multiple teams at Berkshire Classic | Stockbridge Country Club | 11:30 AM |
| Girls Soccer | Oct 13 | Pittsfield at Taconic | BCC | 01:00 PM |
| |
| Boys Soccer | Oct 14 | Drury at Belchertown | | 01:30 PM |
| Boys Soccer | Oct 14 | McCann Tech at Smith Voc. | | 04:00 PM |
| co-ed Volleyball | Oct 14 | Mount Greylock at Amherst | | 06:00 PM |
| |
| Boys Soccer | Oct 15 | Monument Mountain at Mahar | | 04:00 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 | Lee at Mount Greylock | | 03:30 PM |
| co-ed Golf | Oct 15 | Hoosac Valley at Monument Mountain | | 03:30 PM |
| co-ed Volleyball | Oct 15 | Pittsfield at Mt. Anthony (VT) | | 05:45 PM |
| Girls Soccer | Oct 15 | Lenox at Drury | | 04:30 PM |
| Girls Soccer | Oct 15 | Mount Greylock at Lee | | 04:30 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 |
| co-ed Cross Country | Oct 16 | Taconic at Mount Everett | | 04:30 PM |
| co-ed Cross Country | Oct 16 | Wahconah at Mount Everett | | 04:30 PM |
| co-ed Cross Country | Oct 16 | Pittsfield at Mount Greylock | | 04:30 PM |
| co-ed Cross Country | Oct 16 | Lenox at Mount Greylock | | 04:30 PM |
| co-ed Cross Country | Oct 16 | Monument Mountain at Mount Everett | | 04:30 PM |
| co-ed Golf | Oct 16 | Wahconah at Mount Greylock | | 03:30 PM |
| co-ed Volleyball | Oct 16 | Mount Greylock at Lee | | 06:00 PM |
| co-ed Volleyball | Oct 16 | Wahconah at Monument Mountain | | 06:00 PM |
| Girls Soccer | Oct 16 | McCann Tech at Westfield Tech | | 04:00 PM |
| |
| Boys Soccer | Oct 17 | Putnam at McCann Tech | | 04:00 PM |
| Boys Soccer | Oct 17 | Taconic at Drury | | 04:30 PM |
| co-ed Golf | Oct 17 | Pittsfield at Mount Greylock | | 03:30 PM |
| Girls Soccer | Oct 17 | Pittsfield at Hoosac Valley | | 04:30 PM |
| Girls Soccer | Oct 17 | Mount Greylock at Monument Mountain | | 06:00 PM |
| |
| Boys Soccer | Oct 18 | Pittsfield at Lenox | | 06:00 PM |
| Boys Soccer | Oct 18 | Monument Mountain at Pope Francis | | 06:00 PM |
| co-ed Volleyball | Oct 18 | Mount Greylock at Pittsfield | | 05:45 PM |
| co-ed Volleyball | Oct 18 | Taconic at Monument Mountain | | 06:00 PM |
| Football | Oct 18 | Easthampton at Monument Mountain | | 07:00 PM |
| Football | Oct 18 | Pittsfield at Amherst | | 07:00 PM |
| Football | Oct 18 | Taconic at Putnam | Central High | 07:00 PM |
| Girls Soccer | Oct 18 | Pittsfield at Drury | | 04:00 PM |
| Girls Soccer | Oct 18 | St Mary’s at McCann Tech | | 04:00 PM |
| |
| Boys Soccer | Oct 19 | Pittsfield at Southwick | | 02:00 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 |
| 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 |
| Girls Soccer | Oct 21 | Lee at Drury | | 04:00 PM |
| Girls Soccer | Oct 21 | Taconic at Mount Everett | | 04:30 PM |
| Girls Soccer | Oct 21 | Wahconah at Mount Greylock | | 04:30 PM |
| Girls Soccer | Oct 21 | Monument Mountain at Hoosac Valley | | 04:30 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 | Pittsfield at Tantasqua | | 06:00 PM |
| Girls Soccer | Oct 22 | Commerce at McCann Tech | | 04:00 PM |
| Girls Soccer | Oct 22 | Pittsfield at Springfield Central | | 04:00 PM |
| |
| co-ed Volleyball | Oct 23 | Mount Greylock at Mount Everett | | 06:00 PM |
| co-ed Volleyball | Oct 23 | Lenox at Pittsfield | | 06:00 PM |
| co-ed Volleyball | Oct 23 | S. Hadley at Taconic | | 06:00 PM |
| Girls Soccer | Oct 23 | Mount Greylock at Mount Everett | | 04:15 PM |
| |
| Boys Soccer | Oct 24 | McCann Tech at P.V.C.S. | | 04:00 PM |
| co-ed Volleyball | Oct 24 | Hampden Charter at Pittsfield | | 06:00 PM |
| co-ed Volleyball | Oct 24 | Lee at Taconic | | 06:00 PM |
| |
| Boys Soccer | Oct 25 | Mount Everett at Drury | | 04:00 PM |
| Boys Soccer | Oct 25 | Taconic at Hoosac Valley | | 04:00 PM |
| Boys Soccer | Oct 25 | Mount Greylock at Lenox | | 06:00 PM |
| Boys Soccer | Oct 25 | Pittsfield at Monument Mountain | | 06:00 PM |
| Boys Soccer | Oct 25 | Lenox at Monument Mountain | | 06:00 PM |
| Football | Oct 25 | Putnam at Pittsfield | BCC | 06:00 PM |
| Football | Oct 25 | Drury at Ware | | 07:00 PM |
| Football | Oct 25 | Monument Mountain at Greenfield | | 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 | 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 |
| |
| Boys Soccer | Oct 28 | Pope Francis at Drury | | 04:00 PM |
| Boys Soccer | Oct 28 | Frontier at Mount Greylock | | 06:30 PM |
| co-ed Volleyball | Oct 28 | Lenox at Taconic | | 06:00 PM |
| Girls Soccer | Oct 28 | Monument Mountain at Westfield | | 04:00 PM |
| Girls Soccer | Oct 28 | Hampden Charter School of Science at McCann Tech | | 04:00 PM |
| Girls Soccer | Oct 28 | Drury at Mount Everett | | 04:30 PM |
| Girls Soccer | Oct 28 | Mount Greylock at Hoosac Valley | | 04:30 PM |
| Girls Soccer | Oct 28 | Pittsfield at Wahconah | | 04:30 PM |
| Girls Soccer | Oct 28 | Taconic at Lenox | | 06:00 PM |
| |
| Boys Soccer | Oct 29 | Monument Mountain at Belchertown | | 04:00 PM |
| Boys Soccer | Oct 29 | Pittsfield at Shepherd Hill | | 06:00 PM |
| |
| Girls Soccer | Oct 30 | Mahar at Mount Greylock | | 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 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 |
