| Sport | Date | Teams | Location | Time |
| Boys Soccer | Sep 27 | Putnam at McCann Tech | | 04:00 PM |
| Boys Soccer | Sep 27 | Hoosac Valley at P.V.C.S. | | 04:00 PM |
| Boys Soccer | Sep 27 | Taconic at Gateway | | 04:00 PM |
| Boys Soccer | Sep 27 | Pittsfield at Westfield | | 04:30 PM |
| Boys Soccer | Sep 27 | Agawam at Monument Mountain | | 04:30 PM |
| Boys Soccer | Sep 27 | Pope Francis at Mount Greylock | | 05:00 PM |
| co-ed Golf | Sep 27 | Monument Mountain at Mount Everett | | 03:30 PM |
| co-ed Golf | Sep 27 | Taconic at Mount Greylock | | 03:30 PM |
| co-ed Golf | Sep 27 | Hoosac Valley at Wahconah | | 03:30 PM |
| co-ed Volleyball | Sep 27 | Easthampton at Lenox | | 06:00 PM |
| co-ed Volleyball | Sep 27 | Pittsfield at Taconic | | 06:00 PM |
| co-ed Volleyball | Sep 27 | Wahconah at Lee | | 06:30 PM |
| Girls Soccer | Sep 27 | Drury at Taconic | | 04:00 PM |
| Girls Soccer | Sep 27 | Lee at Hampden Charter School of Science | | 04:00 PM |
| Girls Soccer | Sep 27 | Hopkins at Mount Everett | | 04:30 PM |
| Girls Soccer | Sep 27 | Chicopee at Lenox | | 06:30 PM |
| Girls Soccer | Sep 27 | Granby at Monument Mountain | | 06:30 PM |
| |
| Boys Soccer | Sep 28 | Mount Everett at Wahconah | | 07:00 PM |
| co-ed Cross Country | Sep 28 | McCann Tech at Hampshire | | 04:00 PM |
| co-ed Golf | Sep 28 | McCann Tech at Springfield Central | | 03:00 PM |
| co-ed Golf | Sep 28 | Mount Greylock at Lee | | 03:30 PM |
| co-ed Volleyball | Sep 28 | Mount Greylock at E. Longmeadow | | 06:00 PM |
| co-ed Volleyball | Sep 28 | Monument Mountain at Paulo Friere | | 06:00 PM |
| co-ed Volleyball | Sep 28 | Granby at Taconic | | 06:30 PM |
| co-ed Volleyball | Sep 28 | Mahar at Wahconah | | 06:30 PM |
| Girls Soccer | Sep 28 | Monument Mountain at Mount Greylock | | 04:30 PM |
| Girls Soccer | Sep 28 | Wahconah at Longmeadow | | 06:30 PM |
| Girls Soccer | Sep 28 | Pittsfield at Chicopee Comp | | 07:00 PM |
| |
| Boys Soccer | Sep 29 | Hoosac Valley at Drury | | 04:00 PM |
| Boys Soccer | Sep 29 | Commerce at Taconic | | 05:00 PM |
| co-ed Cross Country | Sep 29 | Multiple teams at Hoosac Valley | | 04:00 PM |
| co-ed Golf | Sep 29 | Mount Greylock at Taconic | | 03:30 PM |
| co-ed Golf | Sep 29 | Lenox at Mount Everett | | 03:30 PM |
| co-ed Volleyball | Sep 29 | Mount Everett at Taconic | | 06:00 PM |
| co-ed Volleyball | Sep 29 | Pittsfield at Westfield | | 06:00 PM |
| co-ed Volleyball | Sep 29 | Frontier at Lee | | 06:00 PM |
| Girls Soccer | Sep 29 | Pittsfield at Westfield | | 04:00 PM |
| Girls Soccer | Sep 29 | Pioneer Valley at Lee | | 04:30 PM |
| Girls Soccer | Sep 29 | Hoosac Valley at Mahar | | 04:30 PM |
| Girls Soccer | Sep 29 | Drury at Mount Everett | | 04:30 PM |
| Girls Soccer | Sep 29 | Lenox at Northampton | | 07:00 PM |
| Girls Soccer | Sep 29 | Taconic at Hampden Charter School of Science | Time TBA | 12:00 AM |
| |
| Boys Soccer | Sep 30 | Mount Everett at Palmer | | 04:30 PM |
| Boys Soccer | Sep 30 | Lenox at S. Hadley | | 06:15 PM |
| Boys Soccer | Sep 30 | Easthampton at Wahconah | | 07:00 PM |
| co-ed Golf | Sep 30 | Wahconah at Taconic | | 03:30 PM |
| co-ed Volleyball | Sep 30 | Monument Mountain at Taconic | | 06:00 PM |
| co-ed Volleyball | Sep 30 | Lenox at Mount Greylock | | 06:00 PM |
| co-ed Volleyball | Sep 30 | Franklin Tech at Wahconah | | 06:30 PM |
| Girls Soccer | Sep 30 | Westfield Tech at McCann Tech | | 04:00 PM |
| Girls Soccer | Sep 30 | Mt. Anthony (VT) at Mount Greylock | | 04:00 PM |
| Girls Soccer | Sep 30 | Wahconah at Hoosac Valley | | 04:00 PM |
| |
| Boys Soccer | Oct 01 | Taconic at Westfield Tech | | 04:00 PM |
| Boys Soccer | Oct 01 | Drury at P.V.C.S. | | 04:00 PM |
| Boys Soccer | Oct 01 | Lenox at Mount Greylock | | 06:30 PM |
| Boys Soccer | Oct 01 | McCann Tech at Hoosac Valley | Renfrew | 07:00 PM |
| co-ed Golf | Oct 01 | Mount Greylock at Wahconah | | 03:30 PM |
| co-ed Golf | Oct 01 | Lee at Lenox | | 03:30 PM |
| co-ed Golf | Oct 01 | Taconic at Monument Mountain | | 04:00 PM |
| co-ed Volleyball | Oct 01 | Lee at Mount Greylock | | 06:00 PM |
| co-ed Volleyball | Oct 01 | Mount Everett at Mt. Anthony (VT) | | 06:00 PM |
| Football | Oct 01 | Hoosac Valley at Easthampton | | 07:00 PM |
| Football | Oct 01 | Wahconah at E. Longmeadow | | 07:00 PM |
| Football | Oct 01 | Taconic at Ludlow | | 07:00 PM |
| Football | Oct 01 | Lee at Frontier | | 07:00 PM |
| Football | Oct 01 | Pittsfield at Putnam | | 08:00 PM |
| Girls Soccer | Oct 01 | Taconic at Mount Everett | | 04:00 PM |
| Girls Soccer | Oct 01 | Hopkins at Lee | | 04:00 PM |
| Girls Soccer | Oct 01 | S. Hadley at Pittsfield | | 04:00 PM |
| Girls Soccer | Oct 01 | Gateway at Drury | | 04:00 PM |
| Girls Soccer | Oct 01 | Ware at Hoosac Valley | | 05:00 PM |
| |
| Boys Soccer | Oct 02 | Monument Mountain at Ludlow | | 11:55 AM |
| Boys Soccer | Oct 02 | Wahconah at Mount Everett | Time TBA | 12:00 PM |
| Football | Oct 02 | McCann Tech at Drury | | 01:00 PM |
| Girls Soccer | Oct 02 | Pittsfield at Minnechaug | | 04:00 PM |
| Girls Soccer | Oct 02 | Brattleboro at Wahconah | | 04:00 PM |
| Girls Soccer | Oct 02 | Lenox at Monument Mountain | | 06:00 PM |
| |
| Boys Soccer | Oct 04 | McCann Tech at P.V.C.S. | | 04:00 PM |
| Boys Soccer | Oct 04 | Taconic at Putnam | | 04:00 PM |
| Boys Soccer | Oct 04 | Westfield Tech at Drury | | 04:00 PM |
| Boys Soccer | Oct 04 | Gateway at Hoosac Valley | | 04:30 PM |
| Boys Soccer | Oct 04 | Mount Everett at S. Hadley | | 04:30 PM |
| Boys Soccer | Oct 04 | Lenox at Mahar | | 04:30 PM |
| Boys Soccer | Oct 04 | Frontier at Wahconah | | 07:00 PM |
| co-ed Golf | Oct 04 | Mohawk at McCann Tech | | 03:00 PM |
| co-ed Golf | Oct 04 | Hoosac Valley at Mount Greylock | | 03:30 PM |
| co-ed Volleyball | Oct 04 | Monument Mountain at Mount Everett | | 06:00 PM |
| co-ed Volleyball | Oct 04 | Pittsfield at Lee | | 06:00 PM |
| co-ed Volleyball | Oct 04 | Taconic at Science and Technology | | 06:00 PM |
| co-ed Volleyball | Oct 04 | Mount Greylock at Chicopee | | 06:00 PM |
| co-ed Volleyball | Oct 04 | Turners Falls at Wahconah | | 06:30 PM |
| Girls Soccer | Oct 04 | Chinese Immersion Charter at McCann Tech | | 04:00 PM |
| Girls Soccer | Oct 04 | Wahconah at Pittsfield | | 04:00 PM |
| |
| Boys Soccer | Oct 05 | Pittsfield at Monument Mountain | | 04:30 PM |
| Boys Soccer | Oct 05 | Mount Greylock at Westfield | | 05:00 PM |
| co-ed Cross Country | Oct 05 | Pioneer at McCann Tech | Greylock Glen | 04:00 PM |
| co-ed Golf | Oct 05 | Hoosac Valley at Lenox | | 03:30 PM |
| Girls Soccer | Oct 05 | Taconic at Gateway | | 04:00 PM |
| Girls Soccer | Oct 05 | Putnam at McCann Tech | | 04:00 PM |
| Girls Soccer | Oct 05 | Drury at Lee | | 04:30 PM |
| Girls Soccer | Oct 05 | Mount Everett at Hampden Charter School of Science | | 04:30 PM |
| Girls Soccer | Oct 05 | Springfield Central at Mount Greylock | | 04:30 PM |
| Girls Soccer | Oct 05 | Hoosac Valley at Palmer | | 06:00 PM |
| Girls Soccer | Oct 05 | Granby at Lenox | | 06:30 PM |
| Girls Soccer | Oct 05 | Hampshire at Wahconah | | 07:00 PM |
| |
| Boys Soccer | Oct 06 | McCann Tech at Drury | | 04:00 PM |
| Boys Soccer | Oct 06 | Mahar at Mount Everett | | 04:30 PM |
| Boys Soccer | Oct 06 | Commerce at Hoosac Valley | | 05:00 PM |
| Boys Soccer | Oct 06 | Lenox at Wahconah | | 07:00 PM |
| co-ed Cross Country | Oct 06 | Multiple teams at Mount Everett | | 04:00 PM |
| co-ed Cross Country | Oct 06 | Multiple teams at Lee | | 04:00 PM |
| co-ed Golf | Oct 06 | Sabis at McCann Tech | | 03:00 PM |
| co-ed Golf | Oct 06 | Taconic at Lenox | | 03:30 PM |
| co-ed Golf | Oct 06 | Mount Greylock at Monument Mountain | | 03:30 PM |
| co-ed Volleyball | Oct 06 | Monument Mountain at Mount Greylock | | 06:00 PM |
| co-ed Volleyball | Oct 06 | Wahconah at Lee | | 06:00 PM |
| co-ed Volleyball | Oct 06 | Taconic at Pittsfield | | 06:00 PM |
| co-ed Volleyball | Oct 06 | Mt. Anthony (VT) at Lenox | | 06:00 PM |
| |
| co-ed Golf | Oct 07 | Taconic at Hoosac Valley | | 03:30 PM |
| co-ed Golf | Oct 07 | Mount Everett at Wahconah | | 03:30 PM |
| co-ed Volleyball | Oct 07 | Mount Everett at Housatonic Valley RHS | | 05:30 PM |
| co-ed Volleyball | Oct 07 | Lee at S. Hadley | | 06:15 PM |
| Girls Soccer | Oct 07 | Smith Vocational at McCann Tech | | 04:00 PM |
| Girls Soccer | Oct 07 | Pioneer Valley at Drury | | 04:00 PM |
| Girls Soccer | Oct 07 | Hampshire at Pittsfield | | 04:30 PM |
| Girls Soccer | Oct 07 | Gateway at Mount Everett | | 04:30 PM |
| Girls Soccer | Oct 07 | Ware at Mount Greylock | | 05:00 PM |
| Girls Soccer | Oct 07 | Southwick at Monument Mountain | | 06:00 PM |
| Girls Soccer | Oct 07 | Hoosac Valley at Springfield Central | | 06:00 PM |
| Girls Soccer | Oct 07 | Lee at Taconic | | 06:00 PM |
| Girls Soccer | Oct 07 | Northampton at Lenox | | 06:30 PM |
| Girls Soccer | Oct 07 | Wahconah at Chicopee Comp | | 07:00 PM |
| |
| Boys Soccer | Oct 08 | Wahconah at S. Hadley | | 04:00 PM |
| Boys Soccer | Oct 08 | Gateway at Drury | | 04:00 PM |
| Boys Soccer | Oct 08 | Lenox at Easthampton | | 04:00 PM |
| Boys Soccer | Oct 08 | Westfield Tech at McCann Tech | | 04:00 PM |
| Boys Soccer | Oct 08 | Mount Everett at Frontier | | 04:30 PM |
| Boys Soccer | Oct 08 | Agawam at Pittsfield | | 04:30 PM |
| Boys Soccer | Oct 08 | Monument Mountain at Mount Greylock | | 06:30 PM |
| Boys Soccer | Oct 08 | Taconic at Hoosac Valley | Time TBA | 12:00 AM |
| co-ed Golf | Oct 08 | Lenox at Wahconah | | 03:30 PM |
| co-ed Volleyball | Oct 08 | Lenox at Sabis | | 05:15 PM |
| co-ed Volleyball | Oct 08 | Mount Greylock at Belchertown | | 06:00 PM |
| co-ed Volleyball | Oct 08 | Mount Everett at Springfield Central | | 06:00 PM |
| co-ed Volleyball | Oct 08 | Ware at Monument Mountain | | 06:00 PM |
| co-ed Volleyball | Oct 08 | Mohawk at Wahconah | | 06:30 PM |
| co-ed Volleyball | Oct 08 | Putnam at Taconic | | 06:30 PM |
| Football | Oct 08 | Chicopee at Pittsfield | | 05:00 PM |
| Football | Oct 08 | Monument Mountain at Smith Vocational | | 06:00 PM |
| Football | Oct 08 | Commerce at Lee | | 07:00 PM |
| Football | Oct 08 | Wahconah at Agawam | | 07:00 PM |
| Football | Oct 08 | Putnam at Taconic | | 08:00 PM |
| |
| Boys Soccer | Oct 09 | Monument Mountain at Mount Everett | | 02:00 PM |
| Football | Oct 09 | Pathfinder at McCann Tech | | 01:00 PM |
| Football | Oct 09 | Frontier at Hoosac Valley | | 01:30 PM |
| Girls Soccer | Oct 09 | Granby at Mount Greylock | | 01:30 PM |
| Girls Soccer | Oct 09 | Monument Mountain at Wahconah | | 06:00 PM |
| Girls Soccer | Oct 09 | Lenox at Hoosac Valley | | 11:00 AM |
| |
| co-ed Golf | Oct 10 | Multiple teams at Berkshire Classic | Stockbridge Golf Club | 10:00 AM |
| |
| co-ed Golf | Oct 11 | Mount Everett at Lee | | 03:30 PM |
| co-ed Golf | Oct 11 | Mount Greylock at Lenox | | 03:30 PM |
| co-ed Volleyball | Oct 11 | Mount Greylock at Mt. Anthony (VT) | | 06:00 PM |
| Girls Soccer | Oct 11 | Monument Mountain at Northampton | | 04:00 PM |
| |
| Boys Soccer | Oct 12 | Lenox at Mount Everett | | 04:30 PM |
| Boys Soccer | Oct 12 | P.V.C.S. at Hoosac Valley | | 04:30 PM |
| Boys Soccer | Oct 12 | Pittsfield at Mount Greylock | | 06:30 PM |
| co-ed Golf | Oct 12 | McCann Tech at St Mary’s | | 03:00 PM |
| co-ed Golf | Oct 12 | Taconic at Wahconah | | 03:30 PM |
| co-ed Track & Field | Oct 12 | Greenfield at Wahconah | | 06:25 PM |
| co-ed Volleyball | Oct 12 | Belchertown at Lenox | | 06:00 PM |
| co-ed Volleyball | Oct 12 | Holyoke at Mount Everett | | 06:00 PM |
| co-ed Volleyball | Oct 12 | Taconic at Ware | | 06:00 PM |
| co-ed Volleyball | Oct 12 | Monument Mountain at Putnam | | 06:30 PM |
| Girls Soccer | Oct 12 | McCann Tech at Commerce | | 04:00 PM |
| Girls Soccer | Oct 12 | Mount Greylock at Drury | | 04:00 PM |
| Girls Soccer | Oct 12 | Longmeadow at Pittsfield | | 04:30 PM |
| Girls Soccer | Oct 12 | S. Hadley at Wahconah | | 07:00 PM |
| |
| Boys Soccer | Oct 13 | McCann Tech at Gateway | | 04:00 PM |
| Boys Soccer | Oct 13 | Hoosac Valley at Putnam | | 04:00 PM |
| Boys Soccer | Oct 13 | Drury at Commerce | | 04:00 PM |
| Boys Soccer | Oct 13 | P.V.C.S. at Taconic | | 05:00 PM |
| Boys Soccer | Oct 13 | Pope Francis at Monument Mountain | | 06:00 PM |
| co-ed Cross Country | Oct 13 | Multiple teams at Mount Greylock | | 04:00 PM |
| co-ed Cross Country | Oct 13 | Multiple teams at Lenox | | 04:30 PM |
| co-ed Golf | Oct 13 | Lee at Hoosac Valley | | 03:30 PM |
| co-ed Golf | Oct 13 | Taconic at Mount Everett | | 03:30 PM |
| co-ed Volleyball | Oct 13 | Lenox at Mount Everett | | 06:00 PM |
| co-ed Volleyball | Oct 13 | Pittsfield at West Springfield | | 06:00 PM |
| co-ed Volleyball | Oct 13 | Mount Greylock at Taconic | | 06:00 PM |
| co-ed Volleyball | Oct 13 | Lee at Chicopee Comp | | 06:15 PM |
| Girls Cross Country | Oct 13 | McCann Tech at Hampden Charter | | 04:00 PM |
| Girls Soccer | Oct 13 | Drury at Hopkins | | 04:00 PM |
| Girls Soccer | Oct 13 | Monson at Lenox | | 04:00 PM |
| Girls Soccer | Oct 13 | Chicopee at Monument Mountain | | 04:00 PM |
| Girls Soccer | Oct 13 | Taconic at Pioneer | | 04:00 PM |
| Girls Soccer | Oct 13 | Mount Everett at Lee | | 04:30 PM |
| |
| Boys Soccer | Oct 14 | Mount Greylock at Chicopee | | 06:00 PM |
| Boys Soccer | Oct 14 | Frontier at Lenox | | 06:30 PM |
| co-ed Golf | Oct 14 | Lee at Taconic | | 03:30 PM |
| co-ed Volleyball | Oct 14 | Holyoke at Monument Mountain | | 06:00 PM |
| co-ed Volleyball | Oct 14 | Westfield at Lee | | 06:00 PM |
| Girls Soccer | Oct 14 | McCann Tech at Science and Technology | | 04:00 PM |
| Girls Soccer | Oct 14 | Mahar at Hoosac Valley | | 04:30 PM |
| Girls Soccer | Oct 14 | Agawam at Wahconah | | 07:00 PM |
| |
| Boys Soccer | Oct 15 | Commerce at McCann Tech | | 04:00 PM |
| Boys Soccer | Oct 15 | Drury at Taconic | | 04:00 PM |
| Boys Soccer | Oct 15 | Monument Mountain at Wahconah | | 07:00 PM |
| co-ed Volleyball | Oct 15 | Wahconah at Athol | | 05:15 PM |
| co-ed Volleyball | Oct 15 | Sabis at Mount Greylock | | 06:00 PM |
| co-ed Volleyball | Oct 15 | Taconic at Springfield Central | | 06:00 PM |
| co-ed Volleyball | Oct 15 | Ware at Mount Everett | | 06:00 PM |
| co-ed Volleyball | Oct 15 | Lenox at E. Longmeadow | | 06:00 PM |
| co-ed Volleyball | Oct 15 | Chic Comp at Pittsfield | | 06:00 PM |
| Football | Oct 15 | McCann Tech at Monument Mountain | | 06:00 PM |
| Football | Oct 15 | Pittsfield at S. Hadley | | 07:00 PM |
| Football | Oct 15 | Drury at Pathfinder | | 07:00 PM |
| Football | Oct 15 | Taconic at Chicopee | | 07:00 PM |
| Football | Oct 15 | Hoosac Valley at Belchertown | | 07:00 PM |
| Football | Oct 15 | Wahconah at Amherst-Pelham Reg High School | | 07:00 PM |
| Girls Soccer | Oct 15 | Monument Mountain at Monson | | 04:00 PM |
| Girls Soccer | Oct 15 | Drury at Hampden Charter School of Science | | 04:00 PM |
| Girls Soccer | Oct 15 | Lenox at Southwick | | 04:00 PM |
| Girls Soccer | Oct 15 | Springfield Central at Hoosac Valley | | 04:30 PM |
| Girls Soccer | Oct 15 | Pioneer at Mount Everett | | 04:30 PM |
| Girls Soccer | Oct 15 | Lee at Gateway | | 05:00 PM |
| Girls Soccer | Oct 15 | Mount Greylock at Palmer | | 05:00 PM |
| Girls Soccer | Oct 15 | Hopkins at Taconic | | 06:30 PM |
| |
| Boys Soccer | Oct 16 | Mount Everett at Easthampton | | 01:00 PM |
| Football | Oct 16 | Easthampton at Lee | | 07:00 PM |
| Girls Soccer | Oct 16 | Taconic at Pittsfield | | 01:00 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 Volleyball | Oct 18 | Mount Everett at Science and Technology | | 05:00 PM |
| co-ed Volleyball | Oct 18 | Pittsfield at Agawam | | 06:00 PM |
| co-ed Volleyball | Oct 18 | Mount Greylock at Easthampton | | 06:00 PM |
| co-ed Volleyball | Oct 18 | Monument Mountain at Science and Technology | | 06:00 PM |
| co-ed Volleyball | Oct 18 | Chicopee at Lenox | | 06:00 PM |
| co-ed Volleyball | Oct 18 | West Springfield at Lee | | 06:00 PM |
| co-ed Volleyball | Oct 18 | Pioneer Valley at Wahconah | | 06:30 PM |
| Girls Soccer | Oct 18 | Pittsfield at Agawam | | 04:30 PM |
| Girls Soccer | Oct 18 | Mount Everett at Hopkins | | 04:30 PM |
| Girls Soccer | Oct 18 | Wahconah at Hampshire | | 06:30 PM |
| Girls Soccer | Oct 18 | Mount Greylock at Hoosac Valley | Renfrew | 06:30 PM |
| |
| Boys Soccer | Oct 19 | Drury at Putnam | | 04:00 PM |
| Boys Soccer | Oct 19 | McCann Tech at Taconic | | 04:00 PM |
| Boys Soccer | Oct 19 | Westfield at Hoosac Valley | | 04:30 PM |
| Boys Soccer | Oct 19 | Agawam at Mount Greylock | | 06:30 PM |
| Boys Soccer | Oct 19 | Lenox at Wahconah | | 07:00 PM |
| Boys Soccer | Oct 19 | Monument Mountain at Westfield | | 07:00 PM |
| co-ed Cross Country | Oct 19 | Pope Francis at McCann Tech | Greylock Glen | 04:00 PM |
| Girls Soccer | Oct 19 | Monument Mountain at Granby | | 04:00 PM |
| Girls Soccer | Oct 19 | Taconic at Drury | | 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 | Lenox at Easthampton | | 05:00 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 | Putnam at Mount Everett | | 06:00 PM |
| co-ed Volleyball | Oct 20 | Pittsfield at S. Hadley | | 06:00 PM |
| co-ed Volleyball | Oct 20 | E. Longmeadow at Mount Greylock | | 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 |
| 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 |
| |
| 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 | Agawam at Lee | | 06:00 PM |
| co-ed Volleyball | Oct 22 | Pittsfield at Ludlow | | 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 |
| |
| 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 | W. Springfield at Wahconah | | 07:00 PM |
| Football | Oct 29 | Pittsfield at Ludlow | | 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 Western Mass | Time TBA, Northfield Mtn | 12:00 PM |
