| Sport | Date | Teams | Location | Time |
| Boys Basketball | Jan 28 | Lenox at Monument Mountain | | 07:00 PM |
| Boys Basketball | Jan 28 | Taconic at Drury | | 07:00 PM |
| Boys Basketball | Jan 28 | Mount Greylock at Lee | | 07:30 PM |
| co-ed Bowling | Jan 28 | Multiple teams at Berkshire County League | Greylock Bowl and Golf | 04:00 PM |
| Girls Basketball | Jan 28 | McCann Tech at Ware | | 07:00 PM |
| Girls Basketball | Jan 28 | Lenox at Mount Greylock | | 07:00 PM |
| |
| Boys Basketball | Jan 29 | Pittsfield at Green Tech | Albany | 06:30 PM |
| co-ed Hockey | Jan 29 | Chicopee at Drury | Peter W. Foote | 07:00 PM |
| co-ed Hockey | Jan 29 | Greenfield at Mount Everett | Berkshire School | 07:45 PM |
| Girls Basketball | Jan 29 | Mount Everett at Monson | | 07:00 PM |
| Girls Basketball | Jan 29 | John J. Duggan Academy at Lee | | 07:00 PM |
| |
| Boys Basketball | Jan 30 | Pathfinder at McCann Tech | | 07:00 PM |
| Boys Basketball | Jan 30 | Mount Everett at Hampden Charter | | 07:00 PM |
| Boys Basketball | Jan 30 | Wahconah at Taconic | | 08:00 PM |
| co-ed Hockey | Jan 30 | Easthampton at Wahconah | Boys and Girls Club | 07:00 PM |
| Girls Basketball | Jan 30 | Hoosac Valley at Monument Mountain | varsity only | 06:00 PM |
| Girls Basketball | Jan 30 | Wahconah at Taconic | | 06:30 PM |
| Girls Basketball | Jan 30 | Mount Everett at Lenox | | 07:00 PM |
| |
| Boys Basketball | Jan 31 | Monument Mountain at Mount Greylock | | 07:00 PM |
| Boys Basketball | Jan 31 | Lenox at McCann Tech | | 07:00 PM |
| Boys Basketball | Jan 31 | Drury at Lee | | 07:30 PM |
| co-ed Bowling | Jan 31 | Multiple teams at Berkshire County League | Ken's | 04:00 PM |
| Girls Basketball | Jan 31 | McCann Tech at Turners Falls | | 07:00 PM |
| Girls Basketball | Jan 31 | Mount Greylock at Wahconah | | 07:30 PM |
| |
| Boys Basketball | Feb 01 | Longmeadow at Taconic | | 01:00 PM |
| Boys Basketball | Feb 01 | Wahconah at Monument Mountain | | 07:00 PM |
| co-ed Hockey | Feb 01 | Drury at Belchertown | Mullins | 08:30 PM |
| co-ed Skiing | Feb 01 | Multiple teams at Berkshire Nordic League | Wahconah | 10:00 AM |
| co-ed Swimming | Feb 01 | Multiple teams at Berkshire County Individuals | Taconic Hills | 09:00 AM |
| co-ed Wrestling | Feb 01 | Mount Greylock at Eagle Quad (Franklin Tech) | | 09:00 AM |
| co-ed Wrestling | Feb 01 | Mount Everett at Franklin Tech | Time TBA | 12:00 AM |
| Girls Basketball | Feb 01 | Brattleboro at Monument Mountain | | 02:30 PM |
| |
| co-ed Skiing | Feb 03 | Multiple teams at Berkshire County Alpine League | | 05:30 PM |
| Girls Basketball | Feb 03 | Hoosac Valley at Taconic | | 07:00 PM |
| Girls Basketball | Feb 03 | Wahconah at Monument Mountain | | 07:00 PM |
| Girls Basketball | Feb 03 | McCann Tech at Easthampton | | 07:00 PM |
| Girls Basketball | Feb 03 | Drury at Lenox | | 07:00 PM |
| Girls Basketball | Feb 03 | Mount Everett at Frontier | | 07:30 PM |
| Girls Basketball | Feb 03 | Mount Greylock at Lee | | 07:30 PM |
| |
| Boys Basketball | Feb 04 | Lee at Lenox | | 07:00 PM |
| Boys Basketball | Feb 04 | Franklin Tech at McCann Tech | | 07:00 PM |
| Boys Basketball | Feb 04 | Mount Greylock at Mount Everett | | 07:00 PM |
| Boys Basketball | Feb 04 | Hoosac Valley at Pittsfield | | 07:00 PM |
| Boys Basketball | Feb 04 | Drury at Wahconah | | 07:30 PM |
| Girls Basketball | Feb 04 | McCann Tech at Mohawk | | 07:00 PM |
| |
| co-ed Hockey | Feb 05 | Wahconah at Drury | Peter W. Foote | 07:00 PM |
| co-ed Hockey | Feb 05 | Mount Everett at Southwick | | 07:00 PM |
| co-ed Skiing | Feb 05 | Multiple teams at Berkshire County Alpine League | | 05:30 PM |
| Girls Basketball | Feb 05 | Monument Mountain at Pittsfield | | 07:00 PM |
| |
| Boys Basketball | Feb 06 | Mount Everett at Mohawk | | 07:00 PM |
| Girls Basketball | Feb 06 | Lee at Mount Everett | | 07:00 PM |
| Girls Basketball | Feb 06 | McCann Tech at Pathfinder | | 07:00 PM |
| Girls Basketball | Feb 06 | Drury at Mount Greylock | | 07:00 PM |
| Girls Basketball | Feb 06 | Wahconah at Hoosac Valley | | 07:00 PM |
| |
| Boys Basketball | Feb 07 | McCann Tech at Duggan | | 07:00 PM |
| Boys Basketball | Feb 07 | Wahconah at Hoosac Valley | | 07:00 PM |
| Boys Basketball | Feb 07 | Monument Mountain at Lee | | 07:00 PM |
| Boys Basketball | Feb 07 | Taconic at Pittsfield | B & G club | 07:00 PM |
| Boys Basketball | Feb 07 | Bay State Academy at Drury | | 07:00 PM |
| Boys Basketball | Feb 07 | Lenox at Hampden Charter | | 07:00 PM |
| co-ed Bowling | Feb 07 | Multiple teams at Berkshire County League | Ken's | 04:00 PM |
| co-ed Hockey | Feb 07 | Mount Everett at Shepaug | Time TBA | 07:00 PM |
| Girls Basketball | Feb 07 | Taconic at Pittsfield | B & G club | 05:30 PM |
| Girls Basketball | Feb 07 | Drury at Monument Mountain | | 07:00 PM |
| |
| Boys Basketball | Feb 08 | Monument Mountain at Brattleboro | | 02:30 PM |
| Boys Basketball | Feb 08 | Mount Everett at Mount Greylock | | 07:00 PM |
| co-ed Hockey | Feb 08 | Ludlow at Wahconah | Boys and Girls Club | 07:00 PM |
| co-ed Hockey | Feb 08 | Drury at Amherst | Orr | 07:30 PM |
| co-ed Skiing | Feb 08 | Multiple teams at Berkshire Nordic League | Mount Greylock | 10:00 AM |
| |
| Boys Basketball | Feb 09 | Mount Greylock at Sabis | | 02:30 PM |
| |
| Boys Basketball | Feb 10 | Pittsfield at Sabis | | 07:00 PM |
| Boys Basketball | Feb 10 | McCann Tech at Ludlow | | 07:00 PM |
| Boys Basketball | Feb 10 | Taconic at Hoosac Valley | | 07:00 PM |
| Boys Basketball | Feb 10 | Wahconah at Southwick | | 07:00 PM |
| Girls Basketball | Feb 10 | Mount Everett at Mount Greylock | | 07:00 PM |
| Girls Basketball | Feb 10 | Hampden Charter at Lenox | | 07:00 PM |
| Girls Basketball | Feb 10 | Pittsfield at Longmeadow | | 07:00 PM |
| Girls Basketball | Feb 10 | Monument Mountain at Wahconah | | 07:30 PM |
| Girls Basketball | Feb 10 | Drury at Lee | | 07:30 PM |
| |
| Boys Basketball | Feb 11 | Mount Everett at Lenox | | 07:00 PM |
| Girls Basketball | Feb 11 | E. Longmeadow at Taconic | | 06:00 PM |
| Girls Basketball | Feb 11 | Easthampton at McCann Tech | | 07:00 PM |
| |
| Boys Basketball | Feb 12 | Amherst at Wahconah | | 07:00 PM |
| Boys Basketball | Feb 12 | Pittsfield at Longmeadow | | 07:00 PM |
| Boys Basketball | Feb 12 | Monument Mountain at Hoosac Valley | | 07:00 PM |
| Boys Basketball | Feb 12 | McCann Tech at Mount Greylock | | 07:00 PM |
| co-ed Hockey | Feb 12 | Drury at Easthampton | Williston | 06:00 PM |
| |
| Boys Basketball | Feb 13 | Hampden Charter at McCann Tech | | 07:00 PM |
| co-ed Hockey | Feb 13 | S. Hadley at Wahconah | Boys and Girls Club | 07:00 PM |
| Girls Basketball | Feb 13 | Hoosac Valley at Pittsfield | | 07:00 PM |
| Girls Basketball | Feb 13 | Bay State Academy at Mount Greylock | | 07:00 PM |
| Girls Basketball | Feb 13 | Lee at Lenox | | 07:00 PM |
| Girls Basketball | Feb 13 | Drury at Mount Everett | | 07:00 PM |
| Girls Basketball | Feb 13 | Greenfield at Taconic | | 07:00 PM |
| Girls Basketball | Feb 13 | Taconic at Wahconah | | 07:30 PM |
| |
| Boys Basketball | Feb 14 | Drury at Hoosac Valley | | 07:00 PM |
| Boys Basketball | Feb 14 | Mount Everett at Monument Mountain | | 07:00 PM |
| Boys Basketball | Feb 14 | Lenox at Mount Greylock | | 07:00 PM |
| Boys Basketball | Feb 14 | Wahconah at Lee | | 07:30 PM |
| co-ed Bowling | Feb 14 | Multiple teams at Berkshire County League | Cove | 04:00 PM |
| Girls Basketball | Feb 14 | Pope Francis at McCann Tech | | 07:00 PM |
| |
| co-ed Hockey | Feb 15 | Belchertown at Mount Everett | Berkshire School | 06:00 PM |
| co-ed Hockey | Feb 15 | Drury at Southwick | Amelia | 06:00 PM |
| co-ed Hockey | Feb 15 | Wahconah at Easthampton | Williston | 06:30 PM |
| co-ed Skiing | Feb 15 | Multiple teams at Berkshire Nordic League | Berkshire School | 01:00 PM |
| Girls Basketball | Feb 15 | Hoosac Valley at TBA | North/South Crossover, Time TBA, Mount Greylock | 12:00 PM |
| Girls Basketball | Feb 15 | Pittsfield at TBA | North/South Crossover, Time TBA, Mount Greylock | 12:00 PM |
| Girls Basketball | Feb 15 | Lee at TBA | North/South Crossover, Time TBA, Mount Greylock | 12:00 PM |
| Girls Basketball | Feb 15 | Mount Everett at TBA | North/South Crossover, Time TBA, Mount Greylock | 12:00 PM |
| Girls Basketball | Feb 15 | Wahconah at TBA | North/South Crossover, Time TBA, Mount Greylock | 12:00 PM |
| Girls Basketball | Feb 15 | Taconic at TBA | North/South Crossover, Time TBA, Mount Greylock | 12:00 PM |
| Girls Basketball | Feb 15 | TBA at Mount Greylock | North/South Crossover, Time TBA, Mount Greylock | 12:00 PM |
| Girls Basketball | Feb 15 | Drury at TBA | North/South Crossover, Time TBA, Mount Greylock | 12:00 PM |
| Girls Basketball | Feb 15 | Lenox at TBA | North/South Crossover, Time TBA, Mount Greylock | 12:00 PM |
| Girls Basketball | Feb 15 | Monument Mountain at TBA | North/South Crossover, Time TBA, Mount Greylock | 12:00 PM |
| |
| Girls Basketball | Feb 16 | Minnechaug at Taconic | Wachusett | 04:00 PM |
| |
| Boys Basketball | Feb 17 | Hoosac Valley at Taconic | | 07:00 PM |
| Boys Basketball | Feb 17 | Frontier at Drury | | 07:00 PM |
| Boys Basketball | Feb 17 | Granby at Monument Mountain | | 07:00 PM |
| Boys Basketball | Feb 17 | Pittsfield at Wahconah | | 07:00 PM |
| Girls Basketball | Feb 17 | TBA at Taconic | Wachusett | 03:20 AM |
| Girls Basketball | Feb 17 | Mount Greylock at Lenox | | 07:00 PM |
| Girls Basketball | Feb 17 | Pittsfield at Mt. Anthony | | 07:00 PM |
| Girls Basketball | Feb 17 | McCann Tech at Smith Voc. | | 07:00 PM |
| Girls Basketball | Feb 17 | Hoosac Valley at Old Rochester | Time TBA, Foxborough High School | 12:00 PM |
| |
| Boys Basketball | Feb 18 | TBA at Monument Mountain | | 01:00 PM |
| Boys Basketball | Feb 18 | Paulo Freire Social Justice Charter at Lenox | | 07:00 PM |
| Girls Basketball | Feb 18 | McCann Tech at Smith Academy | | 07:00 PM |
| Girls Basketball | Feb 18 | Hoosac Valley at TBA | Time TBA, Foxborough High School | 12:00 PM |
| |
| Boys Basketball | Feb 19 | Pittsfield at Drury | | 07:00 PM |
| co-ed Hockey | Feb 19 | Belchertown at Drury | Peter W. Foote | 07:00 PM |
| co-ed Hockey | Feb 19 | Mount Everett at Easthampton | | 07:00 PM |
| co-ed Hockey | Feb 19 | Wahconah at Ludlow | Olympia | 11:55 AM |
| Girls Basketball | Feb 19 | Lenox at Mount Everett | | 07:00 PM |
| Girls Basketball | Feb 19 | Wahconah at Granby | | 07:00 PM |
| Girls Basketball | Feb 19 | Taconic at Monument Mountain | | 07:00 PM |
| |
| co-ed Skiing | Feb 25 | Multiple teams at State Nordic Ski Meet | Notchview Reservation | 10:00 AM |
| |
| co-ed Bowling | Feb 28 | Multiple teams at Berkshire County Championship | Ken's | 04:00 PM |
| |
| co-ed Skiing | Mar 04 | Multiple teams at State Alpine Ski Meet | Berkshire East | 09:30 AM |
| |
| co-ed Bowling | Mar 07 | Multiple teams at State Championship | Chicopee Lanes | 03:00 PM |
| |
| co-ed Bowling | Mar 08 | Multiple teams at State Championship | Chicopee Lanes | 10:00 AM |
