SCHEDULE
| Sport | Date | Teams | Location | Time |
| Boys Basketball | Dec 09 | Mount Everett at McCann Tech | Franklin Tech tournament | 06:30 PM |
| Boys Basketball | Dec 09 | Taconic at Commerce | 07:00 PM | |
| co-ed Bowling | Dec 09 | Multiple teams at Berkshire County League | Cove | 04:00 PM |
| co-ed Hockey | Dec 09 | McCann Tech at Southwick | 07:00 PM | |
| co-ed Swimming | Dec 09 | Wahconah at Taconic Hills | 04:30 PM | |
| Girls Basketball | Dec 09 | McCann Tech at Mount Everett | Franklin Tech tournament | 03:30 PM |
| Girls Basketball | Dec 09 | Monument Mountain at Belchertown | 07:00 PM | |
| co-ed Hockey | Dec 10 | Mount Everett at McCann Tech | 07:00 PM | |
| co-ed Wrestling | Dec 10 | Mount Greylock at Athol Tournament | 09:00 AM | |
| Boys Basketball | Dec 12 | Pioneer Valley Chinese Immersion at Mount Everett | 05:30 PM | |
| Boys Basketball | Dec 12 | Palmer at Hoosac Valley | 07:00 PM | |
| Boys Basketball | Dec 12 | Drury at Mohawk | 07:00 PM | |
| Boys Basketball | Dec 12 | PVCS at McCann Tech | 07:00 PM | |
| Boys Basketball | Dec 12 | Baystate at Wahconah | 07:00 PM | |
| Boys Basketball | Dec 12 | Lenox at Lee | 07:00 PM | |
| Girls Basketball | Dec 12 | Mount Everett at Lenox | 06:00 PM | |
| Boys Basketball | Dec 13 | Pittsfield at Taconic | Boys and Girls Club | 08:00 PM |
| Girls Basketball | Dec 13 | Hampden Charter at McCann Tech | 06:00 PM | |
| Girls Basketball | Dec 13 | Pittsfield at Taconic | Boys and Girls Club | 06:30 PM |
| Girls Basketball | Dec 13 | Lenox at Lee | 07:00 PM | |
| Girls Basketball | Dec 13 | Hampshire at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Dec 13 | Mount Greylock at Monument Mountain | 07:00 PM | |
| Girls Basketball | Dec 13 | Wahconah at Monson | 07:00 PM | |
| Girls Basketball | Dec 13 | Belchertown at Drury | 07:00 PM | |
| Boys Basketball | Dec 14 | Mount Greylock at Drury | 07:00 PM | |
| co-ed Bowling | Dec 14 | Multiple teams at Berkshire County League | Cove | 04:00 PM |
| co-ed Hockey | Dec 14 | Taconic at McCann Tech | 07:30 PM | |
| co-ed Wrestling | Dec 14 | Monument Mountain at Mount Everett | 06:00 PM | |
| co-ed Wrestling | Dec 14 | Mount Greylock at Taconic | 06:00 PM | |
| Boys Basketball | Dec 15 | Mount Everett at St Mary’s | 06:30 PM | |
| Boys Basketball | Dec 15 | McCann Tech at Pathfinder | 07:00 PM | |
| Boys Basketball | Dec 15 | Hoosac Valley at Monument Mountain | 07:00 PM | |
| co-ed Hockey | Dec 15 | Greenfield at Mount Everett | 07:15 PM | |
| Girls Basketball | Dec 15 | Springfield ICS at Mount Greylock | 06:30 PM | |
| Girls Basketball | Dec 15 | Easthampton at McCann Tech | 07:00 PM | |
| Girls Basketball | Dec 15 | Mount Everett at Lee | 07:00 PM | |
| Girls Basketball | Dec 15 | Lenox at Ware | 07:00 PM | |
| Boys Basketball | Dec 16 | E. Longmeadow at Pittsfield | 05:30 PM | |
| Boys Basketball | Dec 16 | Cape Cod Academy at Wahconah | 07:00 PM | |
| Boys Basketball | Dec 16 | Westfield at Taconic | 07:00 PM | |
| Boys Basketball | Dec 16 | Lee at Mount Greylock | 07:00 PM | |
| Boys Basketball | Dec 16 | Drury at Lenox | 07:00 PM | |
| co-ed Swimming | Dec 16 | Wahconah at New Lebanon | 04:30 PM | |
| Girls Basketball | Dec 16 | South Hadley at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Dec 16 | Pittsfield at Holyoke | 07:00 PM | |
| Boys Basketball | Dec 17 | Cape Cod Academy at Monument Mountain | 05:30 PM | |
| co-ed Hockey | Dec 17 | Mount Everett at Chicopee | Fitzpatrick | 02:00 PM |
| co-ed Hockey | Dec 17 | Taconic at Agawam | Olympia | 02:30 PM |
| co-ed Hockey | Dec 17 | McCann Tech at Easthampton | Lossone | 06:00 PM |
| co-ed Wrestling | Dec 17 | Mount Everett at Knight Hawk Classic | Holyoke HS | 09:00 AM |
| co-ed Wrestling | Dec 17 | Mount Greylock at Knight Hawk Classic | Holyoke HS | 09:00 AM |
| Girls Basketball | Dec 17 | Drury at Monument Mountain | 01:30 PM | |
| Boys Basketball | Dec 19 | Athol at Lee | 07:00 PM | |
| Boys Basketball | Dec 19 | Hoosac Valley at Baystate | 07:00 PM | |
| Boys Basketball | Dec 19 | Hampden Charter at McCann Tech | 07:00 PM | |
| Boys Basketball | Dec 19 | Wahconah at Monument Mountain | 07:00 PM | |
| Boys Basketball | Dec 19 | Taconic at Pope Francis | 07:00 PM | |
| Boys Basketball | Dec 19 | Mount Greylock at Franklin Tech | 07:00 PM | |
| Boys Basketball | Dec 19 | Pittsfield at Westfield | 07:00 PM | |
| Boys Basketball | Dec 19 | Lenox at Greenfield | 07:00 PM | |
| Boys Basketball | Dec 19 | Mount Everett at Duggan | 07:00 PM | |
| Boys Basketball | Dec 19 | Frontier at Drury | 07:00 PM | |
| Girls Basketball | Dec 19 | Drury at Springfield ICS | 06:30 PM | |
| Girls Basketball | Dec 19 | Chicopee Comp at Taconic | 06:30 PM | |
| co-ed Hockey | Dec 20 | Shepaug at Mount Everett | 07:15 PM | |
| Girls Basketball | Dec 20 | McCann Tech at Mount Everett | 05:30 PM | |
| Girls Basketball | Dec 20 | Lee at Renaissance | 06:00 PM | |
| Girls Basketball | Dec 20 | Ludlow at Mount Greylock | 06:30 PM | |
| Girls Basketball | Dec 20 | Hoosac Valley at Amherst | 07:00 PM | |
| Girls Basketball | Dec 20 | Monument Mountain at Pittsfield | 07:00 PM | |
| Girls Basketball | Dec 20 | Wahconah at Granby | 07:00 PM | |
| Girls Basketball | Dec 20 | Lenox at Hopkins | 07:30 PM | |
| Boys Basketball | Dec 21 | Monument Mountain at Drury | 07:00 PM | |
| co-ed Bowling | Dec 21 | Multiple teams at Berkshire County League | Cove | 04:00 PM |
| co-ed Hockey | Dec 21 | Greenfield at McCann Tech | 07:00 PM | |
| co-ed Hockey | Dec 21 | Chicopee at Taconic | 07:30 PM | |
| co-ed Swimming | Dec 21 | Mt. Anthony (VT) at Wahconah | 04:30 PM | |
| Girls Basketball | Dec 21 | Mt. Anthony at Pittsfield | 07:00 PM | |
| Boys Basketball | Dec 22 | Ludlow at Mount Everett | 06:30 PM | |
| Boys Basketball | Dec 22 | Pittsfield at Pope Francis | 07:00 PM | |
| Boys Basketball | Dec 22 | Mount Greylock at Hoosac Valley | 07:00 PM | |
| Boys Basketball | Dec 22 | Duggan at McCann Tech | 07:00 PM | |
| co-ed Hockey | Dec 22 | Belchertown at Mount Everett | 06:00 PM | |
| Girls Basketball | Dec 22 | Wahconah at Holyoke | 07:00 PM | |
| Boys Basketball | Dec 23 | Lenox at Monument Mountain | 07:00 PM | |
| Girls Basketball | Dec 23 | Monument Mountain at Drury | 07:00 PM | |
| Girls Basketball | Dec 23 | Hoosac Valley at Monson | 07:00 PM | |
| Girls Basketball | Dec 23 | Mount Greylock at Agawam | 07:00 PM | |
| Boys Basketball | Dec 27 | Guilderland at Taconic | Colonie HS | 05:30 PM |
| Boys Basketball | Dec 27 | Smith Academy at Mount Greylock | 06:00 PM | |
| Boys Basketball | Dec 27 | Greenfield at Drury | 07:00 PM | |
| Boys Basketball | Dec 27 | Franklin Tech at Lee | 07:00 PM | |
| Boys Basketball | Dec 27 | Pittsfield at Colonie | 07:00 PM | |
| Boys Basketball | Dec 27 | Pioneer Valley at Lenox | 07:00 PM | |
| co-ed Wrestling | Dec 27 | Multiple teams at Berkshire Holiday Tournament | Monument Mountain | 09:00 AM |
| Girls Basketball | Dec 27 | Pittsfield at Hoosac Valley | 07:00 PM | |
| Boys Basketball | Dec 28 | Guilderland at Pittsfield | Colonie HS | 04:30 PM |
| Boys Basketball | Dec 28 | Taconic at Colonie | 06:00 PM | |
| Girls Basketball | Dec 28 | Taconic at Westfield | 04:30 PM | |
| Girls Basketball | Dec 28 | West Springfield at Pittsfield | 05:00 PM | |
| Girls Basketball | Dec 28 | Wahconah at Putnam | 07:00 PM | |
| Boys Basketball | Dec 29 | Renaissance at Wahconah | 06:00 PM | |
| Boys Basketball | Dec 29 | Lee at St Mary’s | 06:30 PM | |
| Boys Basketball | Dec 29 | Monument Mountain at Mount Greylock | 06:30 PM | |
| Girls Basketball | Dec 29 | Easthampton at Mount Everett | 05:30 PM | |
| Girls Basketball | Dec 29 | Mount Greylock at Monson | 06:30 PM | |
| Girls Basketball | Dec 29 | Mahar at Lenox | 07:00 PM | |
| Girls Basketball | Dec 29 | McCann Tech at Pope Francis | 07:00 PM | |
| Girls Basketball | Dec 29 | Lee at Mohawk | 07:00 PM | |
| Boys Basketball | Dec 30 | Amherst at Pittsfield | 02:00 PM | |
| Girls Basketball | Dec 30 | Hampshire at Wahconah | 05:00 PM | |
| Girls Basketball | Dec 30 | Drury at Hoosac Valley | 07:00 PM | |
| co-ed Skiing | Dec 31 | Multiple teams at Berkshire Nordic League | Prospect Mountain | 09:30 AM |
| Boys Basketball | Jan 02 | Palmer at Wahconah | 06:00 PM | |
| Boys Basketball | Jan 02 | Hoosac Valley at Easthampton | 07:00 PM | |
| Boys Basketball | Jan 02 | Taconic at Amherst | 07:00 PM | |
| co-ed Hockey | Jan 02 | McCann Tech at Mount Everett | 07:00 PM | |
| Boys Basketball | Jan 03 | Pittsfield at Mt. Anthony | 07:00 PM | |
| Boys Basketball | Jan 03 | Commerce at Taconic | 07:00 PM | |
| Boys Basketball | Jan 03 | Mount Greylock at Mount Everett | 07:00 PM | |
| Girls Basketball | Jan 03 | Renaissance at Mount Everett | 04:00 PM | |
| Girls Basketball | Jan 03 | Agawam at Mount Greylock | 06:30 PM | |
| Girls Basketball | Jan 03 | Drury at Ludlow | 06:30 PM | |
| Girls Basketball | Jan 03 | Franklin Tech at Lenox | 07:00 PM | |
| Girls Basketball | Jan 03 | Hoosac Valley at Granby | 07:00 PM | |
| Girls Basketball | Jan 03 | Palmer at McCann Tech | 07:00 PM | |
| Girls Basketball | Jan 03 | Pope Francis at Lee | 07:00 PM | |
| Girls Basketball | Jan 03 | Springfield ICS at Monument Mountain | 07:00 PM | |
| co-ed Hockey | Jan 04 | Mount Everett at Easthampton | Lossone | 07:00 PM |
| co-ed Hockey | Jan 04 | Southwick at McCann Tech | 07:30 PM | |
| co-ed Swimming | Jan 04 | New Lebanon at Wahconah | 04:00 PM | |
| co-ed Wrestling | Jan 04 | Mount Greylock at Mount Everett | 06:00 PM | |
| co-ed Wrestling | Jan 04 | Taconic at Monument Mountain | 06:00 PM | |
| co-ed Wrestling | Jan 04 | Taconic at Monument Mountain | 06:00 PM | |
| Girls Basketball | Jan 04 | Springfield Central at Taconic | 07:00 PM | |
| Boys Basketball | Jan 05 | Mohawk at Mount Greylock | 06:00 PM | |
| Boys Basketball | Jan 05 | Easthampton at Monument Mountain | 07:00 PM | |
| Boys Basketball | Jan 05 | Hoosac Valley at Palmer | 07:00 PM | |
| Boys Basketball | Jan 05 | Lee at Turners Falls | 07:00 PM | |
| Boys Basketball | Jan 05 | Mahar at Lenox | 07:00 PM | |
| Boys Basketball | Jan 05 | Taconic at West Springfield | 07:00 PM | |
| Boys Basketball | Jan 05 | Drury at Hopkins | 07:30 PM | |
| Girls Basketball | Jan 05 | Wahconah at Hampshire | 07:00 PM | |
| Boys Basketball | Jan 06 | South Hadley at Wahconah | 07:00 PM | |
| Boys Basketball | Jan 06 | Hampden Charter at McCann Tech | 07:00 PM | |
| co-ed Swimming | Jan 06 | Wahconah at Hudson | 04:30 PM | |
| Girls Basketball | Jan 06 | Lenox at Mount Everett | 05:30 PM | |
| Girls Basketball | Jan 06 | Monson at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Jan 06 | Drury at Mount Greylock | 07:00 PM | |
| Girls Basketball | Jan 06 | McCann Tech at Athol | 07:00 PM | |
| Girls Basketball | Jan 06 | Ware at Lee | 07:00 PM | |
| Girls Basketball | Jan 06 | Taconic at Pittsfield | 07:00 PM | |
| co-ed Hockey | Jan 07 | McCann Tech at South Hadley | Fitzpatrick | 02:00 PM |
| co-ed Hockey | Jan 07 | Mount Everett at Southwick | Amelia | 05:30 PM |
| co-ed Hockey | Jan 07 | Ludlow at Taconic | 06:00 PM | |
| co-ed Skiing | Jan 07 | Multiple teams at Berkshire Nordic League | Mohawk Trail Regional | 10:00 AM |
| Girls Basketball | Jan 07 | Mt. Anthony at Monument Mountain | 03:30 PM | |
| Boys Basketball | Jan 09 | Mount Everett at Westfield Tech | 06:30 PM | |
| Boys Basketball | Jan 09 | McCann Tech at Ludlow | 06:30 PM | |
| Boys Basketball | Jan 09 | Taconic at Pittsfield | Boys and Girls Club | 06:30 PM |
| Boys Basketball | Jan 09 | Wahconah at Baystate | 07:00 PM | |
| Boys Basketball | Jan 09 | Palmer at Monument Mountain | 07:00 PM | |
| Boys Basketball | Jan 09 | South Hadley at Hoosac Valley | 07:00 PM | |
| Boys Bowling | Jan 09 | Springfield ICS at Wahconah | 04:30 PM | |
| co-ed Skiing | Jan 09 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Jan 09 | Lee at Easthampton | 07:00 PM | |
| Girls Basketball | Jan 09 | Lenox at Palmer | 07:00 PM | |
| Girls Basketball | Jan 09 | Mount Everett at Franklin Tech | 07:00 PM | |
| Boys Basketball | Jan 10 | Mount Greylock at Athol | 06:30 PM | |
| Boys Basketball | Jan 10 | Mohawk at Lee | 07:00 PM | |
| Boys Basketball | Jan 10 | Mahar at Drury | 07:00 PM | |
| Boys Basketball | Jan 10 | Lenox at Frontier | 07:30 PM | |
| Girls Basketball | Jan 10 | Monument Mountain at Ludlow | 06:30 PM | |
| Girls Basketball | Jan 10 | Mount Greylock at Springfield ICS | 06:30 PM | |
| Girls Basketball | Jan 10 | Drury at Agawam | 07:00 PM | |
| Girls Basketball | Jan 10 | Pittsfield at Chicopee | 07:00 PM | |
| Girls Basketball | Jan 10 | Taconic at Longmeadow | 07:00 PM | |
| Girls Basketball | Jan 10 | Amherst at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Jan 10 | Granby at Wahconah | 07:00 PM | |
| Boys Basketball | Jan 11 | McCann Tech at Smith Academy | 06:30 PM | |
| Boys Basketball | Jan 11 | St Mary’s at Mount Everett | 06:30 PM | |
| co-ed Hockey | Jan 11 | Ludlow at McCann Tech | 07:00 PM | |
| co-ed Hockey | Jan 11 | Southwick at Taconic | 07:30 PM | |
| co-ed Wrestling | Jan 11 | Monument Mountain at Mount Greylock | 07:00 PM | |
| co-ed Wrestling | Jan 11 | Mount Everett at Taconic | 07:00 PM | |
| Boys Basketball | Jan 12 | Baystate at Monument Mountain | 07:00 PM | |
| Boys Basketball | Jan 12 | Easthampton at Hoosac Valley | 07:00 PM | |
| Boys Basketball | Jan 12 | Agawam at Pittsfield | 07:00 PM | |
| Boys Basketball | Jan 12 | Mount Everett at McCann Tech | 07:00 PM | |
| Boys Basketball | Jan 12 | Lenox at Mount Greylock | 07:00 PM | |
| Boys Basketball | Jan 12 | Wahconah at South Hadley | 07:00 PM | |
| co-ed Swimming | Jan 12 | Wahconah at Pittsfield | 04:30 PM | |
| Girls Basketball | Jan 12 | McCann Tech at Lee | 07:00 PM | |
| Girls Basketball | Jan 12 | Greenfield at Lenox | 07:00 PM | |
| Girls Basketball | Jan 12 | Mount Everett at Southwick | 07:00 PM | |
| Boys Basketball | Jan 13 | Lee at Smith Academy | 06:30 PM | |
| Boys Basketball | Jan 13 | Drury at Pioneer Valley | 07:00 PM | |
| co-ed Hockey | Jan 13 | Mount Everett at Shepaug | Gunn School | 08:30 PM |
| Girls Basketball | Jan 13 | Wahconah at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Jan 13 | Monument Mountain at Mount Greylock | 07:00 PM | |
| Girls Basketball | Jan 13 | Ludlow at Drury | 07:00 PM | |
| Girls Basketball | Jan 13 | Minnechaug at Pittsfield | 07:00 PM | |
| co-ed Hockey | Jan 14 | Taconic at S. Hadley | Fitzpatrick | 02:00 PM |
| co-ed Hockey | Jan 14 | Mount Everett at Greenfield | 06:30 PM | |
| co-ed Hockey | Jan 14 | Easthampton at McCann Tech | 07:00 PM | |
| co-ed Skiing | Jan 14 | Multiple teams at Berkshire Nordic League | Mohawk Trail Regional | 10:00 AM |
| co-ed Wrestling | Jan 14 | Multiple teams at Taconic Invitational | 09:00 AM | |
| Boys Basketball | Jan 16 | Paulo Freire Social Justice Charter at Mount Greylock | 07:00 PM | |
| Boys Basketball | Jan 16 | Drury at Wahconah | 07:30 PM | |
| Girls Basketball | Jan 16 | Mount Everett at Drury | 07:00 PM | |
| Boys Basketball | Jan 17 | Mount Everett at Lenox | 07:00 PM | |
| Boys Basketball | Jan 17 | Pioneer Valley at Hoosac Valley | 07:00 PM | |
| Boys Basketball | Jan 17 | McCann Tech at Lee | 07:00 PM | |
| Girls Basketball | Jan 17 | Renaissance at McCann Tech | 06:00 PM | |
| Girls Basketball | Jan 17 | Mount Greylock at Ludlow | 06:30 PM | |
| Girls Basketball | Jan 17 | Agawam at Monument Mountain | 07:00 PM | |
| Girls Basketball | Jan 17 | West Springfield at Taconic | 07:00 PM | |
| Girls Basketball | Jan 17 | Hoosac Valley at Hampshire | 07:00 PM | |
| Girls Basketball | Jan 17 | Amherst at Wahconah | 07:00 PM | |
| Girls Basketball | Jan 17 | Chicopee Comp at Pittsfield | 07:00 PM | |
| Girls Basketball | Jan 17 | Lee at Southwick | 07:00 PM | |
| Boys Basketball | Jan 18 | Pittsfield at Monument Mountain | 07:00 PM | |
| Boys Basketball | Jan 18 | Chicopee Comp at Taconic | 07:00 PM | |
| co-ed Hockey | Jan 18 | Belchertown at McCann Tech | 07:00 PM | |
| co-ed Hockey | Jan 18 | Mount Everett at Housatonic Valley RHS | Time TBA, South Kent School | 12:00 AM |
| co-ed Skiing | Jan 18 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| co-ed Swimming | Jan 18 | Wahconah at Taconic | 04:30 PM | |
| co-ed Wrestling | Jan 18 | Multiple teams at Berkshire County Duals | 04:00 PM | |
| co-ed Wrestling | Jan 18 | Taconic at Hampshire | 07:00 PM | |
| Girls Basketball | Jan 18 | Drury at Lee | 07:00 PM | |
| Boys Basketball | Jan 19 | Drury at Lee | 07:00 PM | |
| Boys Basketball | Jan 19 | Lenox at Hopkins | 07:30 PM | |
| Girls Basketball | Jan 19 | Mount Everett at Pope Francis | 05:00 PM | |
| Girls Basketball | Jan 19 | Northampton at Taconic | 07:00 PM | |
| Girls Basketball | Jan 19 | Belchertown at Monument Mountain | 07:00 PM | |
| Boys Basketball | Jan 20 | Hampden Charter at Mount Everett | 06:30 PM | |
| Boys Basketball | Jan 20 | Pittsfield at Minnechaug | 07:00 PM | |
| Boys Basketball | Jan 20 | McCann Tech at Westfield Tech | 07:00 PM | |
| Boys Basketball | Jan 20 | Taconic at Agawam | 07:00 PM | |
| Boys Basketball | Jan 20 | Monument Mountain at Wahconah | 07:00 PM | |
| co-ed Swimming | Jan 20 | Hudson at Wahconah | 04:30 PM | |
| Girls Basketball | Jan 20 | Mount Greylock at Mt. Anthony | 07:00 PM | |
| Girls Basketball | Jan 20 | Drury at Taconic | 07:00 PM | |
| Girls Basketball | Jan 20 | E. Longmeadow at Pittsfield | 07:00 PM | |
| Girls Basketball | Jan 20 | Southwick at McCann Tech | 07:00 PM | |
| Girls Basketball | Jan 20 | Renaissance at Lee | 07:00 PM | |
| Girls Basketball | Jan 20 | Lenox at Frontier | 07:30 PM | |
| co-ed Hockey | Jan 21 | Chicopee at McCann Tech | 07:00 PM | |
| co-ed Skiing | Jan 21 | Multiple teams at Berkshire Nordic League | Wahconah HS | 10:00 AM |
| co-ed Wrestling | Jan 21 | Mount Greylock at Mount Everett Duals | 09:00 AM | |
| Girls Basketball | Jan 21 | Wahconah at South Hadley | 05:00 PM | |
| Boys Basketball | Jan 23 | Lee at Hoosac Valley | 07:00 PM | |
| Boys Basketball | Jan 23 | Wahconah at Easthampton | 07:00 PM | |
| co-ed Hockey | Jan 23 | McCann Tech at Amherst | 05:10 PM | |
| co-ed Skiing | Jan 23 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Jan 23 | Southwick at Mount Everett | 05:30 PM | |
| Girls Basketball | Jan 23 | Hoosac Valley at Lee | 07:00 PM | |
| Girls Basketball | Jan 23 | Pittsfield at Westfield | 07:00 PM | |
| Girls Basketball | Jan 23 | Taconic at Holyoke | 07:00 PM | |
| Girls Basketball | Jan 23 | Ware at Lenox | 07:00 PM | |
| Boys Basketball | Jan 24 | Gateway at Mount Everett | 06:30 PM | |
| Boys Basketball | Jan 24 | Smith Voc. at McCann Tech | 07:00 PM | |
| Boys Basketball | Jan 24 | Minnechaug at Taconic | 07:00 PM | |
| Boys Basketball | Jan 24 | Mount Greylock at Lee | 07:00 PM | |
| Boys Basketball | Jan 24 | Lenox at Drury | 07:00 PM | |
| Boys Basketball | Jan 24 | West Springfield at Pittsfield | 07:00 PM | |
| Girls Basketball | Jan 24 | Wahconah at Amherst | 07:00 PM | |
| Girls Basketball | Jan 24 | Monument Mountain at Hampshire | 07:00 PM | |
| Girls Basketball | Jan 24 | Belchertown at Mount Greylock | 07:00 PM | |
| Boys Basketball | Jan 25 | Hoosac Valley at Renaissance | 07:00 PM | |
| co-ed Hockey | Jan 25 | McCann Tech at Taconic | 07:30 PM | |
| co-ed Skiing | Jan 25 | Multiple teams at Berkshire Nordic League | Wahconah HS | 03:30 PM |
| co-ed Swimming | Jan 25 | Taconic Hills at Wahconah | 04:30 PM | |
| Boys Basketball | Jan 26 | Wahconah at Hoosac Valley | 07:00 PM | |
| co-ed Hockey | Jan 26 | Taconic at Ludlow | Olympia | 05:00 PM |
| Girls Basketball | Jan 26 | Drury at Belchertown | 07:00 PM | |
| Girls Basketball | Jan 26 | Mount Everett at McCann Tech | 07:00 PM | |
| Girls Basketball | Jan 26 | Lee at Pope Francis | 07:00 PM | |
| Girls Basketball | Jan 26 | Monument Mountain at Agawam | 07:00 PM | |
| Girls Basketball | Jan 26 | Longmeadow at Taconic | 07:00 PM | |
| Girls Basketball | Jan 26 | Hopkins at Lenox | 07:00 PM | |
| Girls Basketball | Jan 26 | Chicopee at Pittsfield | 07:00 PM | |
| Boys Basketball | Jan 27 | Duggan at Mount Everett | 06:30 PM | |
| Boys Basketball | Jan 27 | Franklin Tech at Mount Greylock | 07:00 PM | |
| Boys Basketball | Jan 27 | South Hadley at Monument Mountain | 07:00 PM | |
| Boys Basketball | Jan 27 | Greenfield at Lenox | 07:00 PM | |
| Boys Basketball | Jan 27 | Lee at Athol | 07:00 PM | |
| Boys Basketball | Jan 27 | Chicopee Comp at Pittsfield | 07:00 PM | |
| Boys Basketball | Jan 27 | McCann Tech at Hampden Charter | 07:00 PM | |
| Boys Basketball | Jan 27 | West Springfield at Taconic | 07:00 PM | |
| Boys Basketball | Jan 27 | Drury at Frontier | 07:30 PM | |
| co-ed Swimming | Jan 27 | Monument Mountain at Wahconah | 04:30 PM | |
| Girls Basketball | Jan 27 | Mount Greylock at Drury | 07:00 PM | |
| co-ed Hockey | Jan 28 | Agawam at Taconic | 06:00 PM | |
| co-ed Hockey | Jan 28 | McCann Tech at Greenfield | 06:30 PM | |
| co-ed Wrestling | Jan 28 | Multiple teams at Mountie Invitational | Mount Greylock | 09:00 AM |
| Girls Basketball | Jan 28 | Taconic at Wahconah | 03:30 PM | |
| Boys Basketball | Jan 30 | Mount Greylock at Smith Academy | 06:30 PM | |
| Boys Basketball | Jan 30 | Wahconah at Pittsfield | 07:00 PM | |
| Boys Basketball | Jan 30 | Lenox at Pioneer Valley | 07:00 PM | |
| Boys Basketball | Jan 30 | Lee at Franklin Tech | 07:00 PM | |
| Boys Basketball | Jan 30 | Drury at Greenfield | 07:00 PM | |
| Boys Basketball | Jan 30 | Monument Mountain at Hoosac Valley | 07:00 PM | |
| co-ed Skiing | Jan 30 | Multiple teams at Berkshire County Alpine League | 05:30 PM | |
| co-ed Swimming | Jan 30 | Springfield ICS at Wahconah | 04:30 PM | |
| Girls Basketball | Jan 30 | Taconic at Springfield Central | 07:00 PM | |
| Girls Basketball | Jan 30 | Drury at Lenox | 07:00 PM | |
| Girls Basketball | Jan 30 | Agawam at Wahconah | 07:00 PM | |
| Girls Basketball | Jan 30 | Pittsfield at Minnechaug | 07:00 PM | |
| Boys Basketball | Jan 31 | Mount Everett at Ludlow | 06:30 PM | |
| Boys Basketball | Jan 31 | McCann Tech at Duggan | 07:00 PM | |
| Girls Basketball | Jan 31 | Monson at Mount Greylock | 06:30 PM | |
| Girls Basketball | Jan 31 | Pope Francis at McCann Tech | 07:00 PM | |
| Girls Basketball | Jan 31 | Amherst at Monument Mountain | 07:00 PM | |
| Girls Basketball | Jan 31 | Frontier at Lenox | 07:00 PM | |
| Girls Basketball | Jan 31 | Springfield ICS at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Jan 31 | Mount Everett at Easthampton | 07:00 PM | |
| Boys Basketball | Feb 01 | Mt. Anthony at Wahconah | 07:00 PM | |
| co-ed Hockey | Feb 01 | Amherst at Taconic | 07:30 PM | |
| co-ed Skiing | Feb 01 | Multiple teams at Berkshire Nordic League | Wahconah | 03:30 PM |
| Boys Basketball | Feb 02 | Mount Greylock at Mohawk | 06:00 PM | |
| Boys Basketball | Feb 02 | Lenox at Mahar | 07:00 PM | |
| Boys Basketball | Feb 02 | Turners Falls at Lee | 07:00 PM | |
| co-ed Hockey | Feb 02 | Southwick at Mount Everett | 06:30 PM | |
| Girls Basketball | Feb 02 | Taconic at West Springfield | 07:00 PM | |
| Girls Basketball | Feb 02 | South Hadley at Drury | 07:00 PM | |
| Girls Basketball | Feb 02 | Pittsfield at Chicopee Comp | 07:00 PM | |
| Boys Basketball | Feb 03 | Westfield Tech at Mount Everett | 06:30 PM | |
| Boys Basketball | Feb 03 | Monson at Monument Mountain | 07:00 PM | |
| Boys Basketball | Feb 03 | Hopkins at Drury | 07:00 PM | |
| Boys Basketball | Feb 03 | Ludlow at McCann Tech | 07:00 PM | |
| Boys Basketball | Feb 03 | Pittsfield at Agawam | 07:00 PM | |
| Boys Basketball | Feb 03 | Wahconah at Belchertown | 07:00 PM | |
| Boys Basketball | Feb 03 | E. Longmeadow at Taconic | 07:00 PM | |
| Boys Basketball | Feb 03 | Hoosac Valley at Hampshire | 07:00 PM | |
| co-ed Hockey | Feb 03 | McCann Tech at Belchertown | 08:30 PM | |
| Girls Basketball | Feb 03 | Lee at Mount Everett | 05:30 PM | |
| Girls Basketball | Feb 03 | Lenox at Mahar | 07:00 PM | |
| Girls Basketball | Feb 03 | Hoosac Valley at Mount Greylock | 07:00 PM | |
| Girls Basketball | Feb 03 | McCann Tech at Southwick | 07:00 PM | |
| co-ed Swimming | Feb 04 | Multiple teams at Berkshire County Individuals | Hudson | 11:00 AM |
| co-ed Hockey | Feb 05 | Easthampton at Mount Everett | 02:00 PM | |
| Boys Basketball | Feb 06 | Hoosac Valley at Wahconah | 07:00 PM | |
| Boys Basketball | Feb 06 | Lee at Lenox | 07:00 PM | |
| Boys Basketball | Feb 06 | Monument Mountain at Palmer | 07:00 PM | |
| co-ed Skiing | Feb 06 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Feb 06 | Pope Francis at Mount Everett | 05:30 PM | |
| Girls Basketball | Feb 06 | Springfield ICS at Drury | 07:00 PM | |
| Girls Basketball | Feb 06 | Lenox at Greenfield | 07:00 PM | |
| Girls Basketball | Feb 06 | Pittsfield at E. Longmeadow | 07:00 PM | |
| Girls Basketball | Feb 06 | Lee at McCann Tech | 07:00 PM | |
| Girls Basketball | Feb 06 | Taconic at Northampton | 07:30 PM | |
| Boys Basketball | Feb 07 | Athol at Mount Greylock | 06:30 PM | |
| Boys Basketball | Feb 07 | McCann Tech at Mount Everett | 07:00 PM | |
| Boys Basketball | Feb 07 | Minnechaug at Pittsfield | 07:00 PM | |
| Boys Basketball | Feb 07 | Agawam at Taconic | 07:00 PM | |
| Boys Basketball | Feb 07 | Frontier at Lenox | 07:00 PM | |
| Boys Basketball | Feb 07 | Lee at Mohawk | 07:00 PM | |
| Boys Basketball | Feb 07 | Drury at Mahar | 07:00 PM | |
| Girls Basketball | Feb 07 | Granby at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Feb 07 | Mount Greylock at Belchertown | 07:00 PM | |
| Girls Basketball | Feb 07 | South Hadley at Wahconah | 07:00 PM | |
| Girls Basketball | Feb 07 | Ludlow at Monument Mountain | 07:00 PM | |
| Boys Basketball | Feb 08 | Monument Mountain at South Hadley | 07:00 PM | |
| co-ed Hockey | Feb 08 | Mount Everett at Taconic | 07:30 PM | |
| co-ed Skiing | Feb 08 | Multiple teams at Berkshire Nordic League | 04:00 PM | |
| Boys Basketball | Feb 09 | Mount Greylock at Turners Falls | 06:30 PM | |
| Girls Basketball | Feb 09 | McCann Tech at Renaissance | 06:00 PM | |
| Girls Basketball | Feb 09 | Monument Mountain at Springfield ICS | 06:30 PM | |
| Girls Basketball | Feb 09 | Hoosac Valley at South Hadley | 07:00 PM | |
| Girls Basketball | Feb 09 | Monson at Wahconah | 07:00 PM | |
| Girls Basketball | Feb 09 | Holyoke at Taconic | 07:00 PM | |
| Girls Basketball | Feb 09 | Agawam at Drury | 07:00 PM | |
| Girls Basketball | Feb 09 | Palmer at Lenox | 07:00 PM | |
| Girls Basketball | Feb 09 | Easthampton at Lee | 07:00 PM | |
| Girls Basketball | Feb 09 | Westfield at Pittsfield | 07:00 PM | |
| Boys Basketball | Feb 10 | Taconic at Minnechaug | 07:00 PM | |
| Boys Basketball | Feb 10 | Mount Everett at Hampden Charter | 07:00 PM | |
| Boys Basketball | Feb 10 | Easthampton at Wahconah | 07:00 PM | |
| Boys Basketball | Feb 10 | Smith Academy at Lee | 07:00 PM | |
| Boys Basketball | Feb 10 | Hoosac Valley at South Hadley | 07:00 PM | |
| Boys Basketball | Feb 10 | Pioneer at Drury | 07:00 PM | |
| Boys Basketball | Feb 10 | Westfield Tech at McCann Tech | 07:00 PM | |
| Boys Basketball | Feb 10 | Pittsfield at West Springfield | 07:00 PM | |
| Girls Basketball | Feb 10 | Mount Greylock at Mahar | 07:00 PM | |
| Girls Basketball | Feb 10 | Lee at Monument Mountain | 07:00 PM | |
| co-ed Hockey | Feb 11 | S. Hadley at Mount Everett | 03:00 PM | |
| co-ed Skiing | Feb 11 | Multiple teams at Berkshire Nordic League | Mount Greylock | 10:00 AM |
| Girls Basketball | Feb 11 | Wahconah at Springfield ICS | 05:30 PM | |
| Boys Basketball | Feb 13 | Taconic at Springfield ICS | 06:30 PM | |
| Boys Basketball | Feb 13 | Wahconah at Palmer | 07:00 PM | |
| Boys Basketball | Feb 13 | Monument Mountain at Easthampton | 07:00 PM | |
| Boys Basketball | Feb 13 | Baystate at Hoosac Valley | 07:00 PM | |
| co-ed Skiing | Feb 13 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Feb 13 | Hampden Charter at McCann Tech | 06:00 PM | |
| Girls Basketball | Feb 13 | Mount Everett at Renaissance | 06:00 PM | |
| Girls Basketball | Feb 13 | Hopkins at Mount Greylock | 06:30 PM | |
| Girls Basketball | Feb 13 | Hoosac Valley at Taconic | 07:00 PM | |
| Girls Basketball | Feb 13 | Southwick at Lee | Time TBA | 12:00 PM |
| Boys Basketball | Feb 14 | Turners Falls at Mount Greylock | 06:30 PM | |
| Boys Basketball | Feb 14 | Hopkins at Lenox | 07:00 PM | |
| co-ed Skiing | Feb 14 | Multiple teams at State Nordic Ski Meet | Prospect Mountain | 11:00 AM |
| Girls Basketball | Feb 14 | Lenox at Monument Mountain | 07:00 PM | |
| Girls Basketball | Feb 14 | Pittsfield at Pope Francis | 07:00 PM | |
| Girls Basketball | Feb 14 | McCann Tech at Easthampton | 07:00 PM | |
| Boys Basketball | Feb 15 | Hoosac Valley at Drury | 07:00 PM | |
| co-ed Hockey | Feb 15 | S. Hadley at Taconic | 07:30 PM | |
| Girls Basketball | Feb 15 | Wahconah at West Springfield | 07:00 PM | |
| co-ed Hockey | Feb 16 | Newtown at Mount Everett | 07:30 PM | |
| co-ed Hockey | Feb 18 | Mount Everett at Ludlow | Olympia | 06:00 PM |
| co-ed Hockey | Feb 18 | Taconic at Easthampton | Lassone | 07:00 PM |
| co-ed Hockey | Feb 18 | Belchertown at McCann Tech | 07:00 PM | |
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