| Sport | Date | Teams | Location | Time |
| Boys Basketball | Dec 10 | Multiple Teams at McCann Tech | Bucky Bullett Jamboree | 05:30 PM |
| |
| co-ed Wrestling | Dec 11 | Mount Everett at Monument Mountain | | 07:00 PM |
| |
| Boys Basketball | Dec 12 | Mount Everett at Ware | Franklin Tech Tourney | 05:00 PM |
| Boys Basketball | Dec 12 | Hoosac Valley at Monument Mountain | | 07:00 PM |
| Boys Basketball | Dec 12 | Lenox at Turners Falls | | 07:00 PM |
| co-ed Hockey | Dec 12 | Drury at Wahconah | Boys and Girls Club | 07:00 PM |
| co-ed Swimming | Dec 12 | Pittsfield at Mt. Anthony (VT) | Bennington Rec | 04:30 PM |
| Girls Basketball | Dec 12 | Mount Everett at Smith Voc. | Franklin Tech Tourney | 06:30 PM |
| Girls Basketball | Dec 12 | Lee at Hoosac Valley | | 07:00 PM |
| Girls Basketball | Dec 12 | Northampton at Pittsfield | | 07:00 PM |
| Girls Basketball | Dec 12 | Mount Greylock at Taconic | | 07:00 PM |
| Girls Basketball | Dec 12 | Monument Mountain at Westfield | | 07:00 PM |
| |
| Boys Basketball | Dec 13 | Mount Everett at TBA | Time TBA, Franklin Tech Tourney | 05:00 PM |
| Boys Basketball | Dec 13 | Pittsfield at Doherty | | 06:30 PM |
| Boys Basketball | Dec 13 | Taconic at St. John Shrewsbury | | 07:00 PM |
| co-ed Bowling | Dec 13 | Multiple teams at Berkshire County League | Cove | 04:00 PM |
| co-ed Swimming | Dec 13 | Monument Mountain at Taconic | YMCA | 04:30 PM |
| Girls Basketball | Dec 13 | Mount Everett at TBA | Time TBA, Franklin Tech Tourney | 03:30 PM |
| Girls Basketball | Dec 13 | Lenox at Frontier | | 07:30 PM |
| |
| Boys Basketball | Dec 14 | Pittsfield at Mahar | Curry Hicks Cage | 01:00 PM |
| Boys Basketball | Dec 14 | Drury at Hopkins Academy | Curry Hicks Cage | 02:30 PM |
| Boys Basketball | Dec 14 | Hoosac Valley at Pioneer | Curry Hicks Cage | 11:15 AM |
| co-ed Hockey | Dec 14 | Mount Everett at S. Hadley | | 04:30 PM |
| co-ed Wrestling | Dec 14 | Mount Greylock at Smith Voc Quad | | 09:00 AM |
| Girls Basketball | Dec 14 | Pittsfield at Wahconah | | 03:30 PM |
| |
| Boys Basketball | Dec 15 | Mount Greylock at Turners Falls | Curry Hicks Cage | 09:30 AM |
| Boys Basketball | Dec 15 | Putnam at Taconic | Curry Hicks Cage | 11:00 AM |
| |
| Boys Basketball | Dec 16 | Hoosac Valley at Lenox | | 07:00 PM |
| Boys Basketball | Dec 16 | Lee at Drury | | 07:00 PM |
| Boys Basketball | Dec 16 | Saint Mary Parish School at Mount Everett | | 07:00 PM |
| Girls Basketball | Dec 16 | Taconic at Hoosac Valley | | 01:00 PM |
| Girls Basketball | Dec 16 | Putnam at Monument Mountain | | 07:00 PM |
| Girls Basketball | Dec 16 | Wahconah at Frontier | | 07:30 PM |
| |
| Boys Basketball | Dec 17 | Longmeadow at Taconic | | 07:00 PM |
| Boys Basketball | Dec 17 | Mount Everett at Hampden Charter | | 07:00 PM |
| Girls Basketball | Dec 17 | Paulo Freire Social Justice Charter at Lenox | | 07:00 PM |
| Girls Basketball | Dec 17 | McCann Tech at Pathfinder | | 07:00 PM |
| Girls Basketball | Dec 17 | Mount Everett at Hoosac Valley | | 07:00 PM |
| Girls Basketball | Dec 17 | Lee at Turners Falls | | 07:00 PM |
| Girls Basketball | Dec 17 | Mount Greylock at Wahconah | | 07:30 PM |
| |
| Boys Basketball | Dec 18 | South Hadley at Mount Greylock | | 07:00 PM |
| Boys Basketball | Dec 18 | Lenox at McCann Tech | | 07:00 PM |
| Boys Basketball | Dec 18 | Hoosac Valley at Lee | | 07:30 PM |
| Boys Basketball | Dec 18 | Monument Mountain at Wahconah | | 07:30 PM |
| co-ed Hockey | Dec 18 | Mount Everett at Drury | Peter W. Foote | 07:00 PM |
| co-ed Swimming | Dec 18 | Pittsfield at Taconic | YMCA | 04:30 PM |
| co-ed Wrestling | Dec 18 | Mount Everett at Taconic | | 07:00 PM |
| Girls Basketball | Dec 18 | Taconic at Pittsfield | | 07:00 PM |
| |
| Boys Basketball | Dec 19 | Mt. Anthony at Pittsfield | B & G club | 05:30 PM |
| Boys Basketball | Dec 19 | Green Tech at Taconic | B & G club | 07:30 PM |
| co-ed Bowling | Dec 19 | Multiple teams at Berkshire County League | Ken's | 04:00 PM |
| co-ed Wrestling | Dec 19 | Mount Greylock at Monument Mountain | | 07:00 PM |
| Girls Basketball | Dec 19 | Monument Mountain at Mt. Anthony | | 07:00 PM |
| Girls Basketball | Dec 19 | Mohawk at McCann Tech | | 07:00 PM |
| Girls Basketball | Dec 19 | Mount Greylock at Mount Everett | | 07:00 PM |
| |
| Boys Basketball | Dec 20 | Hoosac Valley at Mount Greylock | | 07:00 PM |
| Boys Basketball | Dec 20 | Drury at Monument Mountain | | 07:00 PM |
| Boys Basketball | Dec 20 | Mount Everett at Shepaug Valley High | | 07:00 PM |
| Boys Basketball | Dec 20 | Lee at McCann Tech | | 07:30 PM |
| co-ed Swimming | Dec 20 | Taconic at Hudson | | 04:30 PM |
| co-ed Swimming | Dec 20 | Pittsfield at Wahconah | YMCA | 04:30 PM |
| Girls Basketball | Dec 20 | Mount Everett at Drury | | 07:00 PM |
| Girls Basketball | Dec 20 | Pioneer Valley at Lee | | 07:30 PM |
| Girls Basketball | Dec 20 | Lenox at Wahconah | | 07:30 PM |
| Girls Basketball | Dec 20 | Greenfield at Hoosac Valley | Hoosac Holiday Tournament | 07:30 PM |
| |
| co-ed Hockey | Dec 21 | Chicopee at Mount Everett | Berkshire School | 01:00 PM |
| co-ed Hockey | Dec 21 | Drury at Greenfield | | 06:30 PM |
| co-ed Wrestling | Dec 21 | Taconic at Wayland Tournament | | 09:00 AM |
| Girls Basketball | Dec 21 | TBA at Hoosac Valley | Time TBA, Hoosac Holiday Tournament | 06:00 PM |
| |
| co-ed Wrestling | Dec 22 | Mount Everett at Franklin Tech | Time TBA | 12:00 AM |
| |
| Boys Basketball | Dec 23 | Monument Mountain at Mount Everett | | 01:30 PM |
| Boys Basketball | Dec 23 | Wahconah at Mount Greylock | | 05:00 PM |
| Boys Basketball | Dec 23 | Taconic at Lenox | | 07:00 PM |
| Boys Basketball | Dec 23 | Wahconah at Hoosac Valley | | 07:00 PM |
| co-ed Swimming | Dec 23 | Taconic at New Lebanon | | 04:30 PM |
| co-ed Swimming | Dec 23 | Pittsfield at Monument Mountain | Simons Rock | 06:45 PM |
| Girls Basketball | Dec 23 | Monument Mountain at Hoosac Valley | | 07:00 PM |
| Girls Basketball | Dec 23 | Mount Greylock at Drury | | 07:00 PM |
| Girls Basketball | Dec 23 | Mount Everett at Lee | | 07:30 PM |
| |
| Boys Basketball | Dec 27 | Pittsfield at Tantasqua | | 01:00 PM |
| Boys Basketball | Dec 27 | Taconic at Cambridge Rindge | Cathedral High | 01:30 PM |
| Boys Basketball | Dec 27 | Hoosac Valley at Easthampton | | 07:00 PM |
| Boys Basketball | Dec 27 | Shepaug Valley High at Mount Everett | | 07:00 PM |
| Boys Basketball | Dec 27 | McCann Tech at Gateway | | 07:00 PM |
| Boys Basketball | Dec 27 | Monument Mountain at Hampshire | | 07:00 PM |
| Boys Basketball | Dec 27 | Lenox at Drury | | 07:00 PM |
| co-ed Swimming | Dec 27 | New Lebanon at Pittsfield | B & G club | 04:30 PM |
| co-ed Wrestling | Dec 27 | Taconic at Lowell Holiday Tournament | | 06:00 PM |
| co-ed Wrestling | Dec 27 | Multiple teams at Monument Mountain | Berkshire Holiday Tournament | 10:00 AM |
| Girls Basketball | Dec 27 | Lenox at Taconic | | 07:00 PM |
| Girls Basketball | Dec 27 | Lee at Monument Mountain | | 07:30 PM |
| Girls Basketball | Dec 27 | Pittsfield at Troy | Amsterdam Holiday | 11:30 AM |
| |
| Boys Basketball | Dec 28 | Notre Dame at Lenox | | 03:00 PM |
| Boys Basketball | Dec 28 | Wahconah at Sabis | | 05:00 PM |
| Boys Basketball | Dec 28 | Taconic at Acton Boxborough | Cathedral High | 11:55 AM |
| co-ed Hockey | Dec 28 | Amherst at Mount Everett | Berkshire School | 01:00 PM |
| co-ed Hockey | Dec 28 | Easthampton at Drury | Peter W. Foote | 04:00 PM |
| co-ed Wrestling | Dec 28 | Taconic at Lowell Holiday Tournament | | 09:00 AM |
| Girls Basketball | Dec 28 | Drury at Chicopee Comp | | 01:00 PM |
| Girls Basketball | Dec 28 | Pittsfield at Kingston | Amsterdam Holiday | 10:00 AM |
| |
| Boys Basketball | Dec 30 | Mount Greylock at Sabis | | 05:30 PM |
| Boys Basketball | Dec 30 | Pittsfield at Monument Mountain | | 07:00 PM |
| Boys Basketball | Dec 30 | Frontier at Drury | | 07:00 PM |
| Boys Basketball | Dec 30 | Pioneer Valley Christian at McCann Tech | | 07:00 PM |
| Girls Basketball | Dec 30 | McCann Tech at Easthampton | | 07:00 PM |
| Girls Basketball | Dec 30 | Lenox at Lee | | 07:00 PM |
| Girls Basketball | Dec 30 | Taconic at Mount Everett | | 07:00 PM |
| |
| co-ed Skiing | Dec 31 | Multiple teams at Berkshire Nordic League | Prospect Mountain | 10:00 AM |
| Girls Basketball | Dec 31 | Pittsfield at Mount Greylock | | 03:00 PM |
| |
| Boys Basketball | Jan 02 | Pittsfield at Mount Greylock | | 07:00 PM |
| Boys Basketball | Jan 02 | McCann Tech at Franklin Tech | | 07:00 PM |
| co-ed Hockey | Jan 02 | Southwick at Mount Everett | Berkshire School | 03:15 PM |
| Girls Basketball | Jan 02 | Lenox at Monument Mountain | | 07:00 PM |
| Girls Basketball | Jan 02 | Taconic at Belchertown | | 07:00 PM |
| Girls Basketball | Jan 02 | Drury at Hampshire | | 07:00 PM |
| Girls Basketball | Jan 02 | McCann Tech at Pope Francis | | 07:00 PM |
| |
| Boys Basketball | Jan 03 | Lee at Mount Everett | | 07:00 PM |
| Boys Basketball | Jan 03 | Wahconah at Lenox | | 07:00 PM |
| co-ed Bowling | Jan 03 | Multiple teams at Berkshire County League | Ken's | 04:00 PM |
| co-ed Swimming | Jan 03 | Hudson at Pittsfield | YMCA | 04:30 PM |
| co-ed Swimming | Jan 03 | Taconic at Monument Mountain | | 06:45 PM |
| Girls Basketball | Jan 03 | Hoosac Valley at Mount Greylock | | 07:00 PM |
| Girls Basketball | Jan 03 | Pittsfield at E. Longmeadow | | 07:00 PM |
| Girls Basketball | Jan 03 | Lee at McCann Tech | | 07:30 PM |
| |
| Boys Basketball | Jan 04 | Hamden at Taconic | | 02:00 PM |
| co-ed Hockey | Jan 04 | Drury at S. Hadley | Fitzpatrick | 02:30 PM |
| co-ed Hockey | Jan 04 | Mount Everett at Wahconah | Boys and Girls Club | 07:00 PM |
| co-ed Skiing | Jan 04 | Multiple teams at Berkshire Nordic League | Wahconah HS | 10:00 AM |
| co-ed Wrestling | Jan 04 | Mount Greylock at Tiger Duals | | 09:00 AM |
| co-ed Wrestling | Jan 04 | Taconic at Minnechaug Duals | | 09:00 AM |
| co-ed Wrestling | Jan 04 | Mount Everett at Chad Antioch Tournament | Rhode Island | 10:00 AM |
| |
| Boys Basketball | Jan 06 | Taconic at Monument Mountain | | 07:00 PM |
| Boys Basketball | Jan 06 | Paulo Freire Social Justice Charter at Lenox | | 07:00 PM |
| Boys Basketball | Jan 06 | Mount Greylock at Drury | | 07:00 PM |
| Boys Basketball | Jan 06 | Mount Everett at Lee | | 07:30 PM |
| co-ed Skiing | Jan 06 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Jan 06 | Smith Academy at McCann Tech | | 07:00 PM |
| Girls Basketball | Jan 06 | Wahconah at Southwick | | 07:00 PM |
| |
| Boys Basketball | Jan 07 | Duggan at McCann Tech | | 07:00 PM |
| co-ed Swimming | Jan 07 | Monument Mountain at Pittsfield | YMCA | 04:30 PM |
| Girls Basketball | Jan 07 | Mount Everett at Monument Mountain | | 07:00 PM |
| Girls Basketball | Jan 07 | Taconic at Lee | | 07:00 PM |
| Girls Basketball | Jan 07 | Lenox at Hampden Charter | | 07:00 PM |
| Girls Basketball | Jan 07 | Drury at Pittsfield | | 07:00 PM |
| |
| Boys Basketball | Jan 08 | Hoosac Valley at Mohawk | | 06:30 PM |
| Boys Basketball | Jan 08 | Hampden Charter at Lenox | | 07:00 PM |
| Boys Basketball | Jan 08 | Pittsfield at Taconic | | 07:00 PM |
| co-ed Hockey | Jan 08 | Greenfield at Drury | Peter W. Foote | 07:00 PM |
| co-ed Swimming | Jan 08 | Taconic at Mt. Anthony (VT) | | 04:30 PM |
| co-ed Wrestling | Jan 08 | Mount Greylock at Mount Everett | | 07:00 PM |
| Girls Basketball | Jan 08 | Mount Greylock at Westfield | | 06:30 PM |
| |
| Boys Basketball | Jan 09 | Monument Mountain at Lenox | | 07:00 PM |
| Boys Basketball | Jan 09 | Lee at Mount Greylock | | 07:00 PM |
| co-ed Wrestling | Jan 09 | Monument Mountain at Taconic | | 07:00 PM |
| co-ed Wrestling | Jan 09 | Monument Mountain at Taconic | | 07:00 PM |
| Girls Basketball | Jan 09 | Greenfield at McCann Tech | | 07:00 PM |
| |
| Boys Basketball | Jan 10 | Mount Everett at Housatonic Valley | | 06:00 PM |
| Boys Basketball | Jan 10 | McCann Tech at Smith Voc. | | 06:30 PM |
| Boys Basketball | Jan 10 | Drury at Ware | Ware Jr. /Sr. High School | 07:00 PM |
| Boys Basketball | Jan 10 | Holyoke at Pittsfield | | 07:00 PM |
| Boys Basketball | Jan 10 | Phoenix Charter at Hoosac Valley | | 07:00 PM |
| Boys Basketball | Jan 10 | Taconic at Wahconah | | 07:30 PM |
| co-ed Bowling | Jan 10 | Multiple teams at Berkshire County League | Greylock Bowl and Golf | 04:00 PM |
| co-ed Hockey | Jan 10 | Mount Everett at Belchertown | | 07:30 PM |
| co-ed Swimming | Jan 10 | Mt. Anthony (VT) at Pittsfield | B & G club | 04:30 PM |
| Girls Basketball | Jan 10 | Lee at Mount Greylock | | 07:00 PM |
| Girls Basketball | Jan 10 | Pioneer at McCann Tech | | 07:00 PM |
| Girls Basketball | Jan 10 | Wahconah at Mount Everett | | 07:00 PM |
| Girls Basketball | Jan 10 | Taconic at Drury | | 07:00 PM |
| Girls Basketball | Jan 10 | Lenox at Hoosac Valley | | 07:00 PM |
| |
| Boys Basketball | Jan 11 | Bay State Academy at Pittsfield | | 01:30 PM |
| Boys Basketball | Jan 11 | Mount Greylock at Murdock | | 12:30 PM |
| co-ed Hockey | Jan 11 | Drury at Mount Everett | Time TBA, Berkshire School | 04:00 PM |
| co-ed Skiing | Jan 11 | Multiple teams at Berkshire Nordic League | Notchview Reservation | 10:00 AM |
| co-ed Wrestling | Jan 11 | Multiple teams at Taconic Invitational | | 09:30 AM |
| |
| Boys Basketball | Jan 13 | Mount Greylock at Southwick | | 07:00 PM |
| Boys Basketball | Jan 13 | Drury at Taconic | | 07:00 PM |
| Boys Basketball | Jan 13 | St Mary’s at McCann Tech | | 07:00 PM |
| co-ed Hockey | Jan 13 | Mount Everett at Greenfield | | 06:00 PM |
| co-ed Skiing | Jan 13 | Multiple teams at Berkshire County Alpine League | Bousquet | 06:30 PM |
| co-ed Swimming | Jan 13 | Taconic Hills at Taconic | YMCA | 04:30 PM |
| Girls Basketball | Jan 13 | Drury at Hoosac Valley | | 07:00 PM |
| Girls Basketball | Jan 13 | Southwick at Mount Greylock | | 07:00 PM |
| Girls Basketball | Jan 13 | Hopkins Academy at Lenox | | 07:00 PM |
| Girls Basketball | Jan 13 | Pittsfield at Mount Everett | | 07:00 PM |
| Girls Basketball | Jan 13 | Lee at Wahconah | | 07:30 PM |
| |
| Boys Basketball | Jan 14 | Pittsfield at Hoosac Valley | | 07:00 PM |
| Boys Basketball | Jan 14 | Mount Everett at Phoenix Charter | | 07:00 PM |
| Boys Basketball | Jan 14 | Lenox at Lee | | 07:30 PM |
| co-ed Swimming | Jan 14 | Pittsfield at Taconic Hills | Tac Hills | 04:30 PM |
| Girls Basketball | Jan 14 | Burr and Burton at Monument Mountain | | 07:00 PM |
| Girls Basketball | Jan 14 | Mahar at McCann Tech | | 07:00 PM |
| |
| Boys Basketball | Jan 15 | Mount Greylock at McCann Tech | | 07:00 PM |
| Boys Basketball | Jan 15 | Wahconah at Drury | | 07:00 PM |
| co-ed Hockey | Jan 15 | Southwick at Drury | Peter W. Foote | 07:00 PM |
| co-ed Swimming | Jan 15 | Mt. Anthony (VT) at Taconic | YMCA | 04:30 PM |
| co-ed Wrestling | Jan 15 | Monument Mountain at Mount Everett | | 07:00 PM |
| co-ed Wrestling | Jan 15 | Mount Greylock at Taconic | | 07:00 PM |
| Girls Basketball | Jan 15 | Lee at Pittsfield | | 07:00 PM |
| Girls Basketball | Jan 15 | Taconic at Wahconah | | 07:00 PM |
| |
| Boys Basketball | Jan 16 | Chicopee at Taconic | Springfield College | 05:30 PM |
| Boys Basketball | Jan 16 | Lee at Hoosac Valley | | 07:00 PM |
| Boys Basketball | Jan 16 | Ludlow at McCann Tech | | 07:00 PM |
| Girls Basketball | Jan 16 | Pittsfield at Lenox | | 07:00 PM |
| Girls Basketball | Jan 16 | Mount Greylock at Monument Mountain | | 07:00 PM |
| |
| Boys Basketball | Jan 17 | Lenox at Mount Everett | | 07:00 PM |
| Boys Basketball | Jan 17 | Drury at Pittsfield | | 07:00 PM |
| Boys Basketball | Jan 17 | Mount Greylock at Monument Mountain | | 07:00 PM |
| co-ed Bowling | Jan 17 | Multiple teams at Berkshire County League | Cove | 04:00 PM |
| co-ed Hockey | Jan 17 | Easthampton at Mount Everett | Berkshire School | 07:30 PM |
| co-ed Swimming | Jan 17 | Wahconah at Taconic | YMCA | 04:30 PM |
| Girls Basketball | Jan 17 | West Springfield at Taconic | Springfield College | 04:00 PM |
| Girls Basketball | Jan 17 | Hoosac Valley at Millbury | Springfield College - Blake Arena | 05:30 PM |
| Girls Basketball | Jan 17 | Wahconah at Longmeadow | | 07:00 PM |
| Girls Basketball | Jan 17 | McCann Tech at Lee | | 07:30 PM |
| |
| co-ed Skiing | Jan 18 | Multiple teams at Berkshire Nordic League | Mount Greylock | 10:00 AM |
| co-ed Wrestling | Jan 18 | Taconic at Taconic Hills | | 09:00 AM |
| co-ed Wrestling | Jan 18 | Multiple teams at Mount Everett Duals | | 10:00 AM |
| |
| Boys Basketball | Jan 20 | Lee at Monument Mountain | | 07:00 PM |
| Boys Basketball | Jan 20 | Wahconah at Frontier | | 07:30 PM |
| co-ed Hockey | Jan 20 | Chic Comp at Mount Everett | | 03:00 PM |
| Girls Basketball | Jan 20 | Lee at Monument Mountain | | 03:30 PM |
| Girls Basketball | Jan 20 | Lenox at Drury | | 07:00 PM |
| Girls Basketball | Jan 20 | Pittsfield at Hoosac Valley | | 07:00 PM |
| Girls Basketball | Jan 20 | McCann Tech at Mount Greylock | | 07:00 PM |
| |
| Boys Basketball | Jan 21 | Taconic at Mount Greylock | | 07:00 PM |
| Boys Basketball | Jan 21 | Mount Everett at Hoosac Valley | | 07:00 PM |
| Boys Basketball | Jan 21 | McCann Tech at Hampden Charter | | 07:00 PM |
| Boys Basketball | Jan 21 | Lenox at Pittsfield | | 07:00 PM |
| Girls Basketball | Jan 21 | Drury at Wahconah | | 07:30 PM |
| |
| Boys Basketball | Jan 22 | Monument Mountain at Drury | | 07:00 PM |
| co-ed Hockey | Jan 22 | Ludlow at Drury | Peter W. Foote | 07:00 PM |
| co-ed Skiing | Jan 22 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Jan 22 | Amherst-Pelham at Mount Greylock | | 07:00 PM |
| Girls Basketball | Jan 22 | McCann Tech at Hopkins Academy | | 07:30 PM |
| |
| Boys Basketball | Jan 23 | Phoenix Charter at Mount Everett | | 05:30 PM |
| co-ed Hockey | Jan 23 | Chic Comp at Mount Everett | Berkshire School | 07:15 PM |
| Girls Basketball | Jan 23 | Hoosac Valley at Wahconah | | 07:00 PM |
| Girls Basketball | Jan 23 | Pittsfield at Monument Mountain | | 07:00 PM |
| |
| Boys Basketball | Jan 24 | Pope Francis at Taconic | | 07:00 PM |
| Boys Basketball | Jan 24 | Mount Greylock at Lenox | | 07:00 PM |
| Boys Basketball | Jan 24 | Hoosac Valley at Drury | | 07:00 PM |
| Boys Basketball | Jan 24 | McCann Tech at Lee | | 07:30 PM |
| co-ed Bowling | Jan 24 | Multiple teams at Berkshire County League | Ken's | 04:00 PM |
| co-ed Hockey | Jan 24 | Ludlow at Mount Everett | Berkshire School | 07:00 PM |
| co-ed Swimming | Jan 24 | Taconic at Pittsfield | B & G club | 04:30 PM |
| co-ed Wrestling | Jan 24 | Taconic at Berkshire County Duals | Mount Greylock | 04:00 PM |
| Girls Basketball | Jan 24 | Putnam at McCann Tech | | 07:00 PM |
| |
| co-ed Hockey | Jan 25 | Drury at Chic Comp | Fitzpatrick | 04:30 PM |
| co-ed Hockey | Jan 25 | Shepaug at Mount Everett | Berkshire School | 06:30 PM |
| co-ed Wrestling | Jan 25 | Multiple teams at Mountie Invitational | | 09:00 AM |
| co-ed Wrestling | Jan 25 | Northampton at Mount Greylock | | 10:00 AM |
| Girls Basketball | Jan 25 | Drury at Greenfield | Hoosac Valley, Coaches vs. Cancer | 01:30 PM |
| Girls Basketball | Jan 25 | Monument Mountain at Granby | Hoosac Valley, Coaches vs. Cancer | 03:00 PM |
| Girls Basketball | Jan 25 | Wahconah at Quabbin | Hoosac Valley, Coaches vs. Cancer | 04:30 PM |
| Girls Basketball | Jan 25 | Mount Greylock at Hampshire | Hoosac Valley, Coaches vs. Cancer | 06:00 PM |
| Girls Basketball | Jan 25 | Minnechaug at Hoosac Valley | Hoosac Valley, Coaches vs. Cancer | 07:30 PM |
| Girls Basketball | Jan 25 | Lee at Frontier | Hoosac Valley, Coaches vs. Cancer | 10:30 AM |
| Girls Basketball | Jan 25 | Mahar at Lenox | Hoosac Valley, Coaches vs. Cancer | 11:55 AM |
| |
| Boys Basketball | Jan 27 | Saint Mary Parish School at Lee | | 06:30 PM |
| Boys Basketball | Jan 27 | Hoosac Valley at Mt. Anthony | | 07:00 PM |
| Boys Basketball | Jan 27 | McCann Tech at Westfield Tech | | 07:00 PM |
| Boys Basketball | Jan 27 | Wahconah at Pittsfield | | 08:00 PM |
| co-ed Skiing | Jan 27 | Multiple teams at Berkshire County Alpine League | | 05:30 PM |
| Girls Basketball | Jan 27 | Wahconah at Pittsfield | | 06:30 PM |
| Girls Basketball | Jan 27 | Monument Mountain at Taconic | | 07:00 PM |
| Girls Basketball | Jan 27 | Lee at Drury | | 07:00 PM |
| |
| 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 |
| 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 | John J. Duggan Academy at Lee | | 07:00 PM |
| Girls Basketball | Jan 29 | Mount Everett at Monson | | 07:00 PM |
| |
| Boys Basketball | Jan 30 | Wahconah at Taconic | | 06:30 PM |
| Boys Basketball | Jan 30 | Pathfinder at McCann Tech | | 07:00 PM |
| Boys Basketball | Jan 30 | Mount Everett at Hampden Charter | | 07:00 PM |
| Girls Basketball | Jan 30 | Hoosac Valley at Monument Mountain | | 07:00 PM |
| Girls Basketball | Jan 30 | Mount Everett at Lenox | | 07:00 PM |
| Girls Basketball | Jan 30 | Wahconah at Taconic | | 08:00 PM |
| |
| Boys Basketball | Jan 31 | Lenox at McCann Tech | | 07:00 PM |
| Boys Basketball | Jan 31 | Monument Mountain at Mount Greylock | | 07:00 PM |
| Boys Basketball | Jan 31 | Hampden Charter at Mount Everett | | 07:00 PM |
| Boys Basketball | Jan 31 | Drury at Lee | | 07:30 PM |
| co-ed Bowling | Jan 31 | Multiple teams at Berkshire County League | Greylock Bowl and Golf | 04:00 PM |
| Girls Basketball | Jan 31 | McCann Tech at Turners Falls | | 07:00 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 | Mohawk Trail | 10:00 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 | Drury at Lenox | | 07:00 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 | 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 | Hoosac Valley at Pittsfield | | 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 | 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 | Wahconah at Hoosac Valley | | 07:00 PM |
| Girls Basketball | Feb 06 | Drury at Mount Greylock | | 07:00 PM |
| Girls Basketball | Feb 06 | Lee at Mount Everett | | 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 |
| Boys Basketball | Feb 07 | Taconic at Pittsfield | B & G club | 07:00 PM |
| Boys Basketball | Feb 07 | Monument Mountain at Lee | | 07:00 PM |
| Boys Basketball | Feb 07 | McCann Tech at Duggan | | 07:00 PM |
| Boys Basketball | Feb 07 | Hoosac Valley at Wahconah | | 07:30 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 | Drury at Amherst | Orr | 07:30 PM |
| co-ed Skiing | Feb 08 | Multiple teams at Berkshire Nordic League | Mount Greylock | 09:00 PM |
| Girls Basketball | Feb 08 | Monument Mountain at Wahconah | | 05:00 PM |
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| Boys Basketball | Feb 10 | Pittsfield at Sabis | | 07:00 PM |
| Boys Basketball | Feb 10 | Hoosac Valley at Taconic | | 07:00 PM |
| Boys Basketball | Feb 10 | McCann Tech at Ludlow | | 07:00 PM |
| Boys Basketball | Feb 10 | Wahconah at Southwick | | 07:00 PM |
| Girls Basketball | Feb 10 | Hampden Charter at Lenox | | 07:00 PM |
| Girls Basketball | Feb 10 | Mount Everett at Mount Greylock | | 07:00 PM |
| Girls Basketball | Feb 10 | Pittsfield at Longmeadow | | 07:00 PM |
| Girls Basketball | Feb 10 | Drury at Lee | | 07:30 PM |
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| 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 |
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| 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 |
| Girls Basketball | Feb 13 | Bay State Academy at Mount Greylock | | 07:00 PM |
| Girls Basketball | Feb 13 | Hoosac Valley at Pittsfield | | 07:00 PM |
| Girls Basketball | Feb 13 | Greenfield at Taconic | | 07:00 PM |
| Girls Basketball | Feb 13 | Drury at Mount Everett | | 07:00 PM |
| Girls Basketball | Feb 13 | Lee at Lenox | | 07:00 PM |
| |
| Boys Basketball | Feb 14 | Lenox at Mount Greylock | | 07:00 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 | 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 |
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| co-ed Hockey | Feb 15 | Drury at Southwick | Amelia | 06:00 PM |
| co-ed Hockey | Feb 15 | Belchertown at Mount Everett | Berkshire School | 06:00 PM |
| co-ed Skiing | Feb 15 | Multiple teams at Berkshire Nordic League | Berkshire School | 10:00 AM |
| Girls Basketball | Feb 15 | TBA at Pittsfield | TBA | 02:45 AM |
| Girls Basketball | Feb 15 | TBA at Mount Greylock | BC Classic | 07:00 PM |
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| Girls Basketball | Feb 16 | Minnechaug at Taconic | Wachusett | 04:00 PM |
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| Boys Basketball | Feb 17 | Taconic at Hoosac Valley | | 07:00 PM |
| Boys Basketball | Feb 17 | Pittsfield at Wahconah | | 07:00 PM |
| Boys Basketball | Feb 17 | Granby at Monument Mountain | | 07:00 PM |
| Girls Basketball | Feb 17 | TBA at Taconic | Wachusett | 03:20 AM |
| Girls Basketball | Feb 17 | McCann Tech at Smith Voc. | | 07:00 PM |
| 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 | 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 |
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| 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 |
| Girls Basketball | Feb 19 | Wahconah at Granby | | 07:00 PM |
| Girls Basketball | Feb 19 | Lenox at Mount Everett | | 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 | 10:30 AM |
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| co-ed Bowling | Feb 28 | Multiple teams at Berkshire County Championship | Ken's | 04:00 PM |
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| co-ed Skiing | Mar 04 | Multiple teams at State Alpine Ski Meet | Berkshire East | 09:30 AM |
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| co-ed Bowling | Mar 07 | Multiple teams at State Championship | Chicopee Lanes | 03:00 PM |
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| co-ed Bowling | Mar 08 | Multiple teams at State Championship | Chicopee Lanes | 10:00 AM |
