| Sport | Date | Teams | Location | Time |
| Boys Basketball | Jan 27 | Taconic at West Springfield | | 06:00 PM |
| Boys Basketball | Jan 27 | Mount Everett at Duggan | | 07:00 PM |
| Boys Basketball | Jan 27 | Hampden Charter at McCann Tech | | 07:00 PM |
| Girls Basketball | Jan 27 | Easthampton at Mount Everett | | 06:00 PM |
| Girls Basketball | Jan 27 | Agawam at Monument Mountain | | 07:00 PM |
| Girls Basketball | Jan 27 | Mount Greylock at Hoosac Valley | | 07:00 PM |
| Girls Basketball | Jan 27 | Belchertown at Drury | | 07:00 PM |
| Girls Basketball | Jan 27 | Lenox at Frontier | | 07:30 PM |
| |
| Boys Basketball | Jan 28 | Franklin Tech at Lee | | 07:00 PM |
| Boys Basketball | Jan 28 | Pioneer Valley at Lenox | | 07:00 PM |
| Boys Basketball | Jan 28 | Ludlow at McCann Tech | | 07:00 PM |
| Boys Basketball | Jan 28 | Hoosac Valley at Wahconah | | 07:00 PM |
| Boys Basketball | Jan 28 | Smith Academy at Mount Greylock | | 07:00 PM |
| Boys Basketball | Jan 28 | Greenfield at Drury | | 07:00 PM |
| Boys Basketball | Jan 28 | Taconic at Amherst | | 07:30 PM |
| Boys Basketball | Jan 28 | Monument Mountain at South Hadley | | 07:30 PM |
| co-ed Bowling | Jan 28 | Multiple teams at Berkshire County League | Cove | 04:00 PM |
| co-ed Hockey | Jan 28 | Belchertown at Mount Everett | | 07:00 PM |
| co-ed Hockey | Jan 28 | Drury at Wahconah | | 08:15 PM |
| co-ed Swimming | Jan 28 | Wahconah at Monument Mountain | Berkshire South | 05:30 PM |
| Girls Basketball | Jan 28 | Taconic at Longmeadow | | 07:00 PM |
| Girls Basketball | Jan 28 | McCann Tech at Pope Francis | | 07:00 PM |
| Girls Basketball | Jan 28 | Drury at Agawam | | 07:00 PM |
| Girls Basketball | Jan 28 | Pittsfield at Chicopee | | 07:00 PM |
| |
| Boys Basketball | Jan 29 | Drury at Mahar | | 01:30 PM |
| co-ed Skiing | Jan 29 | Multiple teams at Berkshire Nordic League | Wahconah HS | 11:00 AM |
| co-ed Wrestling | Jan 29 | Multiple teams at Mountie Invitational | | 09:00 AM |
| Girls Basketball | Jan 29 | Hoosac Valley at Amherst-Pelham | | 01:00 PM |
| Girls Basketball | Jan 29 | Lee at Pope Francis | | 01:30 PM |
| |
| Boys Basketball | Jan 31 | Ludlow at Mount Everett | | 06:30 PM |
| Boys Basketball | Jan 31 | Pittsfield at Taconic | | 07:00 PM |
| Boys Basketball | Jan 31 | Lee at Turners Falls | | 07:00 PM |
| Boys Basketball | Jan 31 | Mahar at Lenox | | 07:00 PM |
| Boys Basketball | Jan 31 | Hoosac Valley at Monument Mountain | | 07:00 PM |
| Boys Basketball | Jan 31 | Duggan at McCann Tech | | 07:00 PM |
| Boys Basketball | Jan 31 | Drury at Hopkins | | 07:30 PM |
| co-ed Skiing | Jan 31 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Jan 31 | Hampshire at Wahconah | | 07:00 PM |
| Girls Basketball | Jan 31 | McCann Tech at Southwick | | 07:00 PM |
| Girls Basketball | Jan 31 | Lenox at Greenfield | | 07:00 PM |
| |
| Boys Basketball | Feb 01 | Bay State Academy at Wahconah | | 07:00 PM |
| Boys Basketball | Feb 01 | Mount Greylock at Monument Mountain | | 07:00 PM |
| Girls Basketball | Feb 01 | Mount Greylock at Monson | | 06:30 PM |
| Girls Basketball | Feb 01 | Ludlow at Drury | | 06:30 PM |
| Girls Basketball | Feb 01 | Hoosac Valley at Springfield ICS | | 07:00 PM |
| Girls Basketball | Feb 01 | Wahconah at Agawam | | 07:00 PM |
| Girls Basketball | Feb 01 | Mount Everett at Lee | | 07:00 PM |
| Girls Basketball | Feb 01 | Springfield Central at Taconic | | 07:00 PM |
| Girls Basketball | Feb 01 | Monument Mountain at Amherst-Pelham | | 07:30 PM |
| |
| Boys Basketball | Feb 02 | Pope Francis at Taconic | | 07:00 PM |
| Boys Basketball | Feb 02 | McCann Tech at Hampden Charter | | 07:00 PM |
| co-ed Hockey | Feb 02 | Mount Everett at Drury | | 07:00 PM |
| co-ed Wrestling | Feb 02 | Taconic at Ludlow | | 06:00 PM |
| co-ed Wrestling | Feb 02 | Multiple teams at Mass State Dual Meet | TBA | 09:00 AM |
| Girls Basketball | Feb 02 | Southwick at Lee | | 07:00 PM |
| Girls Basketball | Feb 02 | Mahar at Lenox | | 07:00 PM |
| Girls Basketball | Feb 02 | Pope Francis at McCann Tech | | 07:00 PM |
| |
| Boys Basketball | Feb 03 | Westfield Tech at Mount Everett | | 06:30 PM |
| Boys Basketball | Feb 03 | Mount Greylock at Athol | | 06:30 PM |
| Boys Basketball | Feb 03 | Mahar at Drury | | 07:00 PM |
| Boys Basketball | Feb 03 | Taconic at Green Tech | | 07:00 PM |
| Boys Basketball | Feb 03 | McCann Tech at Ludlow | | 07:00 PM |
| Boys Basketball | Feb 03 | Agawam at Pittsfield | | 07:00 PM |
| Boys Basketball | Feb 03 | Lenox at Frontier | | 07:30 PM |
| co-ed Hockey | Feb 03 | Drury at Ludlow | Olympia | 06:30 PM |
| Girls Basketball | Feb 03 | Drury at South Hadley | | 07:00 PM |
| Girls Basketball | Feb 03 | Mt. Anthony at Mount Greylock | | 07:00 PM |
| Girls Basketball | Feb 03 | TBA at Lee | | 07:00 PM |
| Girls Basketball | Feb 03 | Monument Mountain at Springfield ICS | | 07:00 PM |
| |
| Boys Basketball | Feb 04 | Hampshire at Hoosac Valley | | 07:00 PM |
| Boys Basketball | Feb 04 | Belchertown at Wahconah | | 07:00 PM |
| Boys Basketball | Feb 04 | West Springfield at Taconic | | 07:00 PM |
| Boys Basketball | Feb 04 | Monument Mountain at Monson | | 07:30 PM |
| co-ed Bowling | Feb 04 | Multiple teams at Berkshire County League | Cove | 04:00 PM |
| Girls Basketball | Feb 04 | Mount Everett at Pope Francis | | 06:00 PM |
| Girls Basketball | Feb 04 | West Springfield at Taconic | | 06:30 PM |
| Girls Basketball | Feb 04 | Chicopee Comp at Pittsfield | | 07:00 PM |
| Girls Basketball | Feb 04 | Drury at Mount Greylock | | 07:00 PM |
| Girls Basketball | Feb 04 | McCann Tech at Lee | | 07:00 PM |
| Girls Basketball | Feb 04 | Greenfield at Lenox | | 07:00 PM |
| |
| Boys Basketball | Feb 05 | Renaissance at Hoosac Valley | | 06:30 PM |
| Boys Basketball | Feb 05 | Lee at Lenox | | 07:00 PM |
| co-ed Hockey | Feb 05 | Mount Everett at Chicopee Comp | Fitzpatrick | 02:00 PM |
| co-ed Hockey | Feb 05 | Wahconah at Amherst-Pelham | Collins/Moylan | 03:30 PM |
| co-ed Skiing | Feb 05 | Multiple teams at Berkshire Nordic League | Mount Greylock | 10:00 AM |
| co-ed Swimming | Feb 05 | Multiple teams at Berkshire County Individuals | Time TBA, New Lebanon High School | 12:00 PM |
| co-ed Wrestling | Feb 05 | Multiple teams at Monument Duals | | 09:00 AM |
| |
| co-ed Hockey | Feb 06 | Drury at Belchertown | | 06:00 PM |
| |
| Boys Basketball | Feb 07 | Wahconah at Hoosac Valley | | 07:00 PM |
| Boys Basketball | Feb 07 | Palmer at Monument Mountain | | 07:00 PM |
| Boys Basketball | Feb 07 | Taconic at Agawam | | 07:00 PM |
| Boys Basketball | Feb 07 | Mount Everett at McCann Tech | | 07:00 PM |
| Boys Basketball | Feb 07 | Pittsfield at Minnechaug | | 07:00 PM |
| Boys Basketball | Feb 07 | Hopkins at Drury | | 07:00 PM |
| co-ed Hockey | Feb 07 | Ludlow at Mount Everett | | 07:45 PM |
| co-ed Skiing | Feb 07 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Feb 07 | McCann Tech at Renaissance | | 06:00 PM |
| Girls Basketball | Feb 07 | Lenox at Palmer | | 07:00 PM |
| Girls Basketball | Feb 07 | Lee at Easthampton | | 07:00 PM |
| |
| Boys Basketball | Feb 08 | Lee at Smith Academy | | 06:30 PM |
| Boys Basketball | Feb 08 | Drury at Pioneer Valley | | 07:00 PM |
| Girls Basketball | Feb 08 | Monument Mountain at Ludlow | | 06:00 PM |
| Girls Basketball | Feb 08 | Renaissance at McCann Tech | | 06:00 PM |
| Girls Basketball | Feb 08 | Belchertown at Mount Greylock | | 06:30 PM |
| Girls Basketball | Feb 08 | Northampton at Taconic | | 07:00 PM |
| Girls Basketball | Feb 08 | Drury at Springfield ICS | | 07:00 PM |
| Girls Basketball | Feb 08 | E. Longmeadow at Pittsfield | | 07:00 PM |
| Girls Basketball | Feb 08 | Hoosac Valley at Granby | | 07:00 PM |
| Girls Basketball | Feb 08 | Wahconah at South Hadley | | 07:00 PM |
| |
| Boys Basketball | Feb 09 | Mount Greylock at Smith Academy | | 06:30 PM |
| Boys Basketball | Feb 09 | Hoosac Valley at Easthampton | | 07:00 PM |
| Boys Basketball | Feb 09 | Monument Mountain at Pittsfield | | 07:30 PM |
| Boys Basketball | Feb 09 | McCann Tech at Lenox | | 07:30 PM |
| co-ed Bowling | Feb 09 | Multiple teams at Berkshire County League | Cove | 04:00 PM |
| co-ed Hockey | Feb 09 | S. Hadley at Wahconah | Location TBA | 04:00 PM |
| co-ed Hockey | Feb 09 | Mount Everett at Easthampton | Lossone | 07:00 PM |
| Girls Basketball | Feb 09 | Mount Everett at Lenox | | 06:00 PM |
| |
| Boys Basketball | Feb 10 | Mount Everett at Hampden Charter | | 06:30 PM |
| Boys Basketball | Feb 10 | Minnechaug at Taconic | | 07:00 PM |
| Boys Basketball | Feb 10 | W. Springfield at Pittsfield | | 07:00 PM |
| Boys Basketball | Feb 10 | McCann Tech at Westfield Tech | | 07:00 PM |
| Girls Basketball | Feb 10 | Springfield ICS at Monument Mountain | | 06:00 PM |
| Girls Basketball | Feb 10 | Renaissance at Mount Everett | | 06:00 PM |
| Girls Basketball | Feb 10 | Lee at Southwick | | 07:00 PM |
| Girls Basketball | Feb 10 | Taconic at Holyoke | | 07:00 PM |
| Girls Basketball | Feb 10 | Agawam at Drury | | 07:00 PM |
| Girls Basketball | Feb 10 | Pittsfield at Westfield | | 07:00 PM |
| Girls Basketball | Feb 10 | South Hadley at Hoosac Valley | | 07:00 PM |
| Girls Basketball | Feb 10 | Wahconah at Monson | | 07:00 PM |
| Girls Basketball | Feb 10 | Mount Greylock at McCann Tech | | 07:00 PM |
| |
| Boys Basketball | Feb 11 | Mount Greylock at Turners Falls | | 06:30 PM |
| Boys Basketball | Feb 11 | Hoosac Valley at South Hadley | | 07:00 PM |
| Boys Basketball | Feb 11 | Easthampton at Wahconah | | 07:00 PM |
| Boys Basketball | Feb 11 | Lenox at Hopkins | | 07:30 PM |
| co-ed Bowling | Feb 11 | Multiple teams at Berkshire County League | Cove | 03:00 PM |
| Girls Basketball | Feb 11 | Lenox at Monument Mountain | | 07:00 PM |
| |
| Boys Basketball | Feb 12 | Brattleboro at Monument Mountain | | 03:30 PM |
| co-ed Hockey | Feb 12 | Mount Everett at Belchertown | Mullins | 05:00 PM |
| co-ed Hockey | Feb 12 | Easthampton at Drury | | 07:00 PM |
| co-ed Hockey | Feb 12 | Chicopee at Wahconah | Location TBA | 07:30 PM |
| co-ed Skiing | Feb 12 | Multiple teams at Berkshire Nordic League | Mount Greylock | 10:00 AM |
| co-ed Swimming | Feb 12 | Multiple teams at Western Mass | Time, place TBA | 12:00 PM |
| co-ed Wrestling | Feb 12 | Multiple teams at Western Mass D3 Tournament | TBA | 09:00 AM |
| Girls Basketball | Feb 12 | Sci-Tech at Taconic | | 01:00 PM |
| Girls Basketball | Feb 12 | Lee at McCann Tech | | 07:00 PM |
| |
| co-ed Swimming | Feb 13 | Multiple teams at Western Mass | Time, place TBA | 12:00 PM |
| Girls Basketball | Feb 13 | Pittsfield at Monument Mountain | | 02:00 PM |
| |
| Boys Basketball | Feb 14 | Mount Greylock at Mahar | | 06:30 PM |
| Boys Basketball | Feb 14 | Pioneer Valley at Drury | | 07:00 PM |
| Boys Basketball | Feb 14 | Easthampton at Monument Mountain | | 07:00 PM |
| Boys Basketball | Feb 14 | Palmer at Wahconah | | 07:00 PM |
| Boys Basketball | Feb 14 | Hoosac Valley at Bay State Academy | Time TBA | 12:00 PM |
| co-ed Skiing | Feb 14 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:00 PM |
| Girls Basketball | Feb 14 | Drury at Mount Everett | | 05:30 PM |
| Girls Basketball | Feb 14 | Mount Greylock at Hopkins | | 06:30 PM |
| Girls Basketball | Feb 14 | Lee at Monument Mountain | | 07:00 PM |
| |
| Boys Basketball | Feb 15 | Lenox at Lee | | 07:00 PM |
| co-ed Skiing | Feb 15 | Multiple teams at State Nordic Ski Meet | Prospect Mountain | 11:00 AM |
| Girls Basketball | Feb 15 | Holyoke at Wahconah | | 07:00 PM |
| Girls Basketball | Feb 15 | Lenox at Franklin Tech | | 07:00 PM |
| Girls Basketball | Feb 15 | Hoosac Valley at Monson | | 07:00 PM |
| |
| Boys Basketball | Feb 16 | McCann Tech at Mount Greylock | | 07:00 PM |
| Boys Basketball | Feb 16 | Pittsfield at Wahconah | | 07:30 PM |
| co-ed Hockey | Feb 16 | Belchertown at Drury | | 07:00 PM |
| co-ed Hockey | Feb 16 | Wahconah at Mount Everett | | 07:45 PM |
| Girls Basketball | Feb 16 | Mount Greylock at Springfield ICS | | 06:30 PM |
| Girls Basketball | Feb 16 | Minnechaug at Pittsfield | | 07:00 PM |
| |
| Boys Basketball | Feb 17 | Hoosac Valley at Pioneer | | 07:00 PM |
| Girls Basketball | Feb 17 | Lee at Lenox | | 07:00 PM |
| |
| co-ed Bowling | Feb 18 | Multiple teams at Berkshire County Championship | | 04:00 PM |
| co-ed Hockey | Feb 18 | Ludlow at Wahconah | Boys and Girls Club | 07:30 PM |
| co-ed Wrestling | Feb 18 | Multiple teams at State D3 Championships | TBA | 09:00 AM |
| |
| co-ed Hockey | Feb 19 | Mount Everett at Greenfield | Collins/Moylan | 06:30 PM |
| co-ed Hockey | Feb 19 | S. Hadley at Drury | | 07:00 PM |
| co-ed Wrestling | Feb 19 | Multiple teams at State D3 Championships | TBA | 09:00 AM |
| |
| co-ed Wrestling | Feb 25 | Multiple teams at All-State Tournament | TBA | 09:00 AM |
| |
| co-ed Wrestling | Feb 26 | Multiple teams at All-State Tournament | TBA | 09:00 AM |
| |
| co-ed Skiing | Mar 01 | Multiple teams at State Alpine Ski Meet | Wachusett Mountain | 10:00 AM |
| |
| co-ed Bowling | Mar 05 | Multiple teams at State Team Championship | Chicopee | 03:00 PM |
| |
| co-ed Bowling | Mar 06 | Multiple teams at State Individual Championships | Chicopee | 10:00 AM |
