SCHEDULE
| Sport | Date | Teams | Location | Time |
| co-ed Bowling | Dec 05 | Multiple teams at Berkshire County League | Cove Lanes | 04:00 PM |
| Girls Basketball | Dec 09 | Multiple Teams at Bucky Bullett Jamboree | Hoosac Valley | 05:00 PM |
| Boys Basketball | Dec 11 | Mount Everett at Hopkins | Franklin Tech Tournament | 03:30 PM |
| Boys Basketball | Dec 11 | Wahconah at Lee | 07:00 PM | |
| Girls Basketball | Dec 11 | Athol at Mount Greylock | Franklin Tech Tournament | 05:00 PM |
| Girls Basketball | Dec 11 | Lee at Lenox | 06:00 PM | |
| Girls Basketball | Dec 11 | Taconic at Hoosac Valley | 06:00 PM | |
| Girls Basketball | Dec 11 | Springfield ICS at Monument Mountain | 07:00 PM | |
| Boys Basketball | Dec 12 | Mount Greylock at Ludlow | 06:30 PM | |
| Boys Basketball | Dec 12 | Longmeadow at Taconic | 07:00 PM | |
| Boys Basketball | Dec 12 | Lenox at Hoosac Valley | 07:00 PM | |
| Boys Basketball | Dec 12 | Greenfield at Drury | 07:00 PM | |
| Boys Basketball | Dec 12 | Mount Everett at TBA | Time TBA, Franklin Tech Tournament | 12:00 PM |
| co-ed Bowling | Dec 12 | Multiple teams at Berkshire County League | Cove Lanes | 04:00 PM |
| co-ed Hockey | Dec 12 | Taconic at Minnechaug | Olympia | 07:10 PM |
| co-ed Swimming | Dec 12 | Hudson at Wahconah | YMCA | 04:30 PM |
| co-ed Swimming | Dec 12 | Taconic at Monument Mountain | Kilpatrick | 06:00 PM |
| Girls Basketball | Dec 12 | McCann Tech at Hampden Charter | 06:00 PM | |
| Girls Basketball | Dec 12 | Mount Everett at Commerce | 06:00 PM | |
| Girls Basketball | Dec 12 | Wahconah at Hampshire | 07:00 PM | |
| Girls Basketball | Dec 12 | Mount Greylock at TBA | Franklin Tech Tournament, Time TBA | 12:00 PM |
| Boys Basketball | Dec 13 | Wahconah at Frontier | UMass Amherst | 12:45 PM |
| co-ed Wrestling | Dec 13 | Monument Mountain at Athol | 09:00 AM | |
| co-ed Wrestling | Dec 13 | Taconic at Athol | 09:00 AM | |
| co-ed Wrestling | Dec 13 | Mount Everett at Holyoke | 09:00 AM | |
| co-ed Wrestling | Dec 13 | Mount Greylock at Holyoke | 09:00 AM | |
| Boys Basketball | Dec 15 | Mount Greylock at Libertas Academy Charter | 06:00 PM | |
| Boys Basketball | Dec 15 | Lenox at Mount Everett | 06:30 PM | |
| Boys Basketball | Dec 15 | Lee at Veritas Prep | 06:30 PM | |
| Boys Basketball | Dec 15 | McCann Tech at Westfield Tech | 07:00 PM | |
| Boys Basketball | Dec 15 | Pittsfield at Drury | 07:00 PM | |
| Boys Basketball | Dec 15 | Taconic at Wahconah | 07:00 PM | |
| Boys Basketball | Dec 15 | Monument Mountain at Hoosac Valley | 07:00 PM | |
| co-ed Swimming | Dec 15 | Mt. Anthony (VT) at Pittsfield | Boys and Girls Club | 04:30 PM |
| Girls Basketball | Dec 15 | Drury at Lee | 07:00 PM | |
| Girls Basketball | Dec 16 | Taconic at Easthampton | 06:00 PM | |
| Girls Basketball | Dec 16 | Pope Francis at Lenox | 06:00 PM | |
| Girls Basketball | Dec 16 | Mount Everett at McCann Tech | 06:00 PM | |
| Girls Basketball | Dec 16 | Frontier at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Dec 16 | PVCS at Monument Mountain | 07:00 PM | |
| co-ed Bowling | Dec 17 | Multiple teams at Berkshire County League | Cove Lanes | 04:00 PM |
| co-ed Hockey | Dec 17 | Amherst at Taconic | Boys and Girls Club | 07:15 PM |
| co-ed Swimming | Dec 17 | Mt. Anthony (VT) at Taconic | YMCA | 04:30 PM |
| co-ed Swimming | Dec 17 | Pittsfield at Monument Mountain | Kilpatrick | 06:00 PM |
| co-ed Wrestling | Dec 17 | Monument Mountain at Mount Everett | 06:00 PM | |
| co-ed Wrestling | Dec 17 | Taconic at Mount Greylock | 06:30 PM | |
| Girls Basketball | Dec 17 | Mount Greylock at Lee | 07:00 PM | |
| Boys Basketball | Dec 18 | Lee at Libertas Academy Charter | 06:00 PM | |
| Boys Basketball | Dec 18 | Mount Everett at Veritas Prep | 06:30 PM | |
| Boys Basketball | Dec 18 | Drury at Taconic | 07:00 PM | |
| Boys Basketball | Dec 18 | Lenox at Mount Greylock | 07:00 PM | |
| Boys Basketball | Dec 18 | Hoosac Valley at Wahconah | 07:00 PM | |
| Boys Basketball | Dec 18 | Turners Falls at McCann Tech | 07:00 PM | |
| Boys Basketball | Dec 19 | Pittsfield at Monument Mountain | 07:00 PM | |
| co-ed Bowling | Dec 19 | Multiple teams at Berkshire County League | K&M Bowling | 04:00 PM |
| co-ed Hockey | Dec 19 | Taconic at Christian Bros. Academy | 04:00 PM | |
| co-ed Hockey | Dec 19 | McCann Tech at Agawam | Olympia | 07:10 PM |
| co-ed Swimming | Dec 19 | Pittsfield at Taconic | YMCA | 04:30 PM |
| co-ed Swimming | Dec 19 | Monument Mountain at Mt. Anthony (VT) | Bennington Rec Center | 04:30 PM |
| Girls Basketball | Dec 19 | PVCS at Mount Greylock | 06:00 PM | |
| Girls Basketball | Dec 19 | South Hadley at Pittsfield | 06:00 PM | |
| Girls Basketball | Dec 19 | McCann Tech at Westfield Tech | 06:00 PM | |
| Girls Basketball | Dec 19 | Monument Mountain at Taconic | 06:00 PM | |
| Girls Basketball | Dec 19 | St Mary’s at Mount Everett | 06:30 PM | |
| Girls Basketball | Dec 19 | Easthampton at Lee | 07:00 PM | |
| Girls Basketball | Dec 19 | Pope Francis at Wahconah | 07:00 PM | |
| Girls Basketball | Dec 19 | Drury at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Dec 19 | Lenox at Frontier | 07:30 PM | |
| Boys Basketball | Dec 20 | St Mary’s at Mount Greylock | 12:30 PM | |
| co-ed Hockey | Dec 20 | McCann Tech at Amherst | Amherst College | 03:00 PM |
| Boys Basketball | Dec 22 | McCann Tech at Pioneer Valley Chinese Immersion | 06:00 PM | |
| Boys Basketball | Dec 22 | Veritas Prep at Mount Greylock | 06:30 PM | |
| Boys Basketball | Dec 22 | Lee at Mount Everett | 06:30 PM | |
| Boys Basketball | Dec 22 | Taconic at Hoosac Valley | 07:00 PM | |
| Boys Basketball | Dec 22 | Wahconah at Pittsfield | 07:00 PM | |
| Boys Basketball | Dec 22 | Wahconah at Pittsfield | 07:00 PM | |
| Boys Basketball | Dec 23 | Drury at Mount Everett | 06:30 PM | |
| Boys Basketball | Dec 23 | Lee at Monument Mountain | 07:00 PM | |
| co-ed Wrestling | Dec 23 | Mount Greylock at Burr and Burton | Time TBA | 12:00 PM |
| Girls Basketball | Dec 23 | Lenox at Wahconah | 06:00 PM | |
| Girls Basketball | Dec 23 | Commerce at McCann Tech | 06:00 PM | |
| Girls Basketball | Dec 23 | Monument Mountain at Mount Greylock | 06:30 PM | |
| Girls Basketball | Dec 23 | Hoosac Valley at Pope Francis | 07:00 PM | |
| Girls Basketball | Dec 23 | Frontier at Drury | 07:00 PM | |
| Girls Basketball | Dec 23 | Taconic at Lee | 07:00 PM | |
| Boys Basketball | Dec 27 | Springfield ICS at Pittsfield | 01:00 PM | |
| co-ed Hockey | Dec 27 | Taconic at McCann Tech | Peter W. Foote | 07:00 PM |
| co-ed Wrestling | Dec 27 | Multiple teams at Berkshire Holiday Tournament | Monument Mountain | 09:00 AM |
| Girls Basketball | Dec 28 | Pittsfield at Hornell School | 08:30 PM | |
| Boys Basketball | Dec 29 | Monument Mountain at Clinton | 05:30 PM | |
| Boys Basketball | Dec 29 | Drury at Mount Greylock | 06:00 PM | |
| Boys Basketball | Dec 29 | Franklin Tech at McCann Tech | 07:00 PM | |
| Boys Basketball | Dec 29 | Lee at Monson | 07:00 PM | |
| Girls Basketball | Dec 29 | Pittsfield at Niskayuna | 05:30 PM | |
| Girls Basketball | Dec 29 | Lee at Wahconah | 06:00 PM | |
| Girls Basketball | Dec 29 | Taconic at Drury | 07:00 PM | |
| Girls Basketball | Dec 29 | Monument Mountain at Hoosac Valley | 07:00 PM | |
| Boys Basketball | Dec 30 | Drury at Veritas Prep | 06:30 PM | |
| Boys Basketball | Dec 30 | Hoosac Valley at Greenfield | 07:00 PM | |
| Boys Basketball | Dec 30 | Taconic at Belchertown | 07:00 PM | |
| Boys Basketball | Dec 30 | Southwick at Lenox | 07:00 PM | |
| Boys Basketball | Dec 30 | Wahconah at John J. Duggan Academy | 07:00 PM | |
| co-ed Hockey | Dec 30 | Taconic at Amherst | Amherst College | 05:00 PM |
| Girls Basketball | Dec 30 | Longmeadow at Pittsfield | 06:00 PM | |
| co-ed Skiing | Dec 31 | Multiple teams at Berkshire Nordic League | Prospect Mountain | 09:30 AM |
| co-ed Hockey | Jan 01 | Taconic at Agawam | Olympia | 08:30 PM |
| Boys Basketball | Jan 02 | McCann Tech at Mount Everett | 06:30 PM | |
| Boys Basketball | Jan 02 | Drury at Monument Mountain | 07:00 PM | |
| Boys Basketball | Jan 02 | Wahconah at Mt. Anthony | 07:00 PM | |
| Boys Basketball | Jan 02 | Pittsfield at Agawam | 07:00 PM | |
| Boys Basketball | Jan 02 | Amherst at Taconic | 07:00 PM | |
| Boys Basketball | Jan 02 | Mount Greylock at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Jan 02 | McCann Tech at Pioneer Valley CICS | 06:00 PM | |
| Girls Basketball | Jan 02 | Taconic at Monson | 06:00 PM | |
| Girls Basketball | Jan 02 | Drury at Pittsfield | 06:00 PM | |
| Girls Basketball | Jan 02 | Hoosac Valley at Mount Greylock | 07:00 PM | |
| co-ed Cross Country | Jan 03 | Multiple teams at Berkshire Nordic League | Mohawk Trail | 10:00 AM |
| co-ed Hockey | Jan 03 | Taconic at Easthampton | Lossone | 07:00 PM |
| co-ed Hockey | Jan 03 | Brattleboro at McCann Tech | Peter W. Foote | 07:00 PM |
| Boys Basketball | Jan 05 | Libertas Academy Charter at Mount Everett | 06:30 PM | |
| Boys Basketball | Jan 05 | Veritas Prep at Lenox | 07:00 PM | |
| Boys Basketball | Jan 05 | Monument Mountain at Taconic | 07:00 PM | |
| Boys Basketball | Jan 05 | Hoosac Valley at Pittsfield | 07:00 PM | |
| Boys Basketball | Jan 05 | Lee at Mount Greylock | 07:00 PM | |
| Boys Basketball | Jan 05 | Smith Voc. at McCann Tech | 07:00 PM | |
| Boys Basketball | Jan 05 | Wahconah at Drury | 07:00 PM | |
| co-ed Swimming | Jan 05 | Taconic at Mt. Anthony (VT) | Bennington Rec Center | 04:30 PM |
| Girls Basketball | Jan 05 | Lenox at Smith Voc. | 06:30 PM | |
| Girls Basketball | Jan 05 | Hampshire at Hoosac Valley | 07:00 PM | |
| Boys Basketball | Jan 06 | Mount Greylock at Southwick | 06:00 PM | |
| Boys Basketball | Jan 06 | Libertas Academy Charter at Lenox | 07:00 PM | |
| co-ed Swimming | Jan 06 | New Lebanon at Pittsfield | Boys and Girls Club | 04:30 PM |
| Girls Basketball | Jan 06 | Minnechaug at Pittsfield | 06:00 PM | |
| Girls Basketball | Jan 06 | Mount Greylock at Taconic | 06:00 PM | |
| Girls Basketball | Jan 06 | Pioneer Valley CICS at Mount Everett | 06:30 PM | |
| Girls Basketball | Jan 06 | Monument Mountain at Easthampton | 07:00 PM | |
| Girls Basketball | Jan 06 | Drury at Pope Francis | 07:00 PM | |
| Girls Basketball | Jan 06 | Lee at PVCS | 07:00 PM | |
| Girls Basketball | Jan 06 | Wahconah at Frontier | 07:30 PM | |
| co-ed Hockey | Jan 07 | Agawam at Taconic | Boys and Girls Club | 07:15 PM |
| co-ed Swimming | Jan 07 | Mt. Anthony (VT) at Wahconah | YMCA | 04:30 PM |
| co-ed Swimming | Jan 07 | Hudson at Monument Mountain | Kilpatrick | 06:00 PM |
| co-ed Wrestling | Jan 07 | Monument Mountain at Taconic | 06:00 PM | |
| co-ed Wrestling | Jan 07 | Mount Everett at Mount Greylock | 07:00 PM | |
| Girls Basketball | Jan 07 | Lenox at Hoosac Valley | 07:00 PM | |
| Boys Basketball | Jan 08 | Monument Mountain at Wahconah | 07:00 PM | |
| Boys Basketball | Jan 08 | Pittsfield at Taconic | Boys and Girls Club | 07:00 PM |
| Boys Basketball | Jan 08 | Mount Everett at Mount Greylock | 07:00 PM | |
| Boys Basketball | Jan 08 | Lenox at Lee | 07:00 PM | |
| Boys Basketball | Jan 08 | Hoosac Valley at Drury | 07:00 PM | |
| co-ed Skiing | Jan 08 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Jan 08 | Pittsfield at Northampton | 07:30 PM | |
| Boys Basketball | Jan 09 | Monument Mountain at South Hadley | 07:00 PM | |
| Boys Basketball | Jan 09 | PVCS at Lee | 07:00 PM | |
| co-ed Bowling | Jan 09 | Multiple teams at Berkshire County League | Cove | 04:00 PM |
| co-ed Swimming | Jan 09 | Wahconah at Taconic | YMCA | 04:30 PM |
| co-ed Swimming | Jan 09 | Taconic Hills at Pittsfield | Boys and Girls Club | 04:30 PM |
| Girls Basketball | Jan 09 | PVCS at Taconic | 06:00 PM | |
| Girls Basketball | Jan 09 | Mount Everett at Westfield Tech | 06:00 PM | |
| Girls Basketball | Jan 09 | Easthampton at Mount Greylock | 06:30 PM | |
| Girls Basketball | Jan 09 | Lenox at Drury | 07:00 PM | |
| Girls Basketball | Jan 09 | Lee at Monument Mountain | 07:00 PM | |
| Girls Basketball | Jan 09 | Gateway at McCann Tech | 07:00 PM | |
| Girls Basketball | Jan 09 | Hoosac Valley at Wahconah | 07:00 PM | |
| co-ed Hockey | Jan 10 | Taconic at Easthampton | Lossone | 03:00 PM |
| co-ed Skiing | Jan 10 | Multiple teams at Berkshire Nordic League | Wahconah | 10:00 AM |
| Boys Basketball | Jan 12 | McCann Tech at Lee | 07:00 PM | |
| Boys Basketball | Jan 12 | Belchertown at Pittsfield | 07:00 PM | |
| co-ed Swimming | Jan 12 | Hudson at Taconic | YMCA | 04:30 PM |
| Girls Basketball | Jan 12 | Lenox at Pope Francis | 06:00 PM | |
| Girls Basketball | Jan 12 | Easthampton at Taconic | 06:00 PM | |
| Girls Basketball | Jan 12 | Commerce at Mount Everett | 06:30 PM | |
| Girls Basketball | Jan 12 | Lee at Mount Greylock | 07:00 PM | |
| Girls Basketball | Jan 12 | Drury at Wahconah | 07:00 PM | |
| Girls Basketball | Jan 12 | Monument Mountain at PVCS | 07:00 PM | |
| Girls Basketball | Jan 12 | Hampden Charter at McCann Tech | 07:00 PM | |
| Girls Basketball | Jan 12 | Hoosac Valley at Frontier | 07:30 PM | |
| Boys Basketball | Jan 13 | Libertas Academy Charter at Mount Greylock | 06:30 PM | |
| Boys Basketball | Jan 13 | Hoosac Valley at Monument Mountain | 07:00 PM | |
| Boys Basketball | Jan 13 | Mohawk at McCann Tech | 07:00 PM | |
| Boys Basketball | Jan 13 | Mount Everett at Lenox | 07:00 PM | |
| Boys Basketball | Jan 13 | Veritas Prep at Lee | 07:00 PM | |
| Boys Basketball | Jan 13 | Drury at Pittsfield | 07:00 PM | |
| Boys Basketball | Jan 13 | Wahconah at Taconic | 07:00 PM | |
| Girls Basketball | Jan 13 | Pittsfield at Springfield Central | 07:00 PM | |
| co-ed Bowling | Jan 14 | Multiple teams at Berkshire County League | Cove | 04:00 PM |
| co-ed Hockey | Jan 14 | McCann Tech at Chicopee | Fitzpatrick | 04:00 PM |
| co-ed Swimming | Jan 14 | Wahconah at Monument Mountain | Kilpatrick | 06:00 PM |
| co-ed Wrestling | Jan 14 | Mount Everett at Taconic | 06:00 PM | |
| co-ed Wrestling | Jan 14 | Mount Greylock at Monument Mountain | 06:00 PM | |
| Boys Basketball | Jan 15 | Monument Mountain at Pittsfield | 07:00 PM | |
| co-ed Skiing | Jan 15 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Jan 15 | Frontier at Lenox | 06:00 PM | |
| Girls Basketball | Jan 15 | McCann Tech at Mount Everett | 06:30 PM | |
| Girls Basketball | Jan 15 | Lee at Easthampton | 07:00 PM | |
| Girls Basketball | Jan 15 | Pittsfield at South Hadley | 07:00 PM | |
| Girls Basketball | Jan 15 | Taconic at Monument Mountain | 07:00 PM | |
| Girls Basketball | Jan 15 | Mount Greylock at PVCS | 07:00 PM | |
| Girls Basketball | Jan 15 | Hoosac Valley at Drury | 07:00 PM | |
| Boys Basketball | Jan 16 | Veritas Prep at Mount Everett | 06:30 PM | |
| Boys Basketball | Jan 16 | Wahconah at Hoosac Valley | 07:00 PM | |
| Boys Basketball | Jan 16 | Westfield Tech at McCann Tech | 07:00 PM | |
| Boys Basketball | Jan 16 | Libertas Academy Charter at Lee | 07:00 PM | |
| Boys Basketball | Jan 16 | Taconic at Drury | 07:00 PM | |
| Boys Basketball | Jan 16 | Mount Greylock at Lenox | 07:00 PM | |
| co-ed Bowling | Jan 16 | Multiple teams at Berkshire County League | King Pins (North Adams) | 04:00 PM |
| co-ed Swimming | Jan 16 | Pittsfield at Wahconah | YMCA | 04:30 PM |
| Girls Basketball | Jan 16 | Ludlow at Mount Greylock | 06:30 PM | |
| Girls Basketball | Jan 16 | Hoosac Valley at South Hadley | 07:00 PM | |
| Girls Basketball | Jan 16 | Drury at Pioneer | 07:00 PM | |
| Boys Basketball | Jan 17 | Staples (Westport, Conn.) at Taconic | Springfield Central, Hoophall | 03:15 PM |
| Boys Basketball | Jan 17 | Niskayuna at Pittsfield | Springfield Central, Hoophall | 11:45 AM |
| Boys Basketball | Jan 17 | Tuckahoe at Monument Mountain | Commerce, Hoophall | 11:45 AM |
| co-ed Skiing | Jan 17 | Multiple teams at Berkshire Nordic League | Notchview Reservation | 10:00 AM |
| Girls Basketball | Jan 17 | Gardiner Area, Maine at Wahconah | SICS, Hoophall Invitational | 01:30 PM |
| Girls Basketball | Jan 17 | Glastonbury, Conn. at Pittsfield | Springfield Central, Hoophall | 01:30 PM |
| Boys Basketball | Jan 18 | Pittsfield at TBA | Time TBA, Springfield Central, Hoophal | 12:00 PM |
| Boys Basketball | Jan 18 | Monument Mountain at TBA | Time TBA, Commerce, Hoophall | 12:00 PM |
| Boys Basketball | Jan 18 | Taconic at TBA | Time TBA, Springfield Central, Hoophall | 12:30 PM |
| Girls Basketball | Jan 18 | Pittsfield at TBA | Time TBA, Springfield Central, Hoophall | 12:00 PM |
| Girls Basketball | Jan 18 | Wahconah at TBA | Time TBA, SICS, Hoophall | 12:00 PM |
| Boys Basketball | Jan 19 | Westfield at Mount Greylock | 01:30 PM | |
| Boys Basketball | Jan 19 | Mount Everett at Hoosac Valley | 06:30 PM | |
| Girls Basketball | Jan 19 | Springfield ICS at Taconic | 06:00 AM | |
| Girls Basketball | Jan 19 | Lenox at Monument Mountain | 07:00 PM | |
| Boys Basketball | Jan 20 | Lenox at Wahconah | 07:00 PM | |
| Boys Basketball | Jan 20 | McCann Tech at Turners Falls | 07:00 PM | |
| Boys Basketball | Jan 20 | Pittsfield at Holyoke | 07:00 PM | |
| Boys Basketball | Jan 20 | Lee at Drury | 07:00 PM | |
| co-ed Swimming | Jan 20 | Taconic at Pittsfield | Boys and Girls Club | 04:30 PM |
| Girls Basketball | Jan 20 | Mount Greylock at Granby | 06:00 PM | |
| Girls Basketball | Jan 20 | Lee at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Jan 20 | Drury at Monument Mountain | 07:00 PM | |
| Boys Basketball | Jan 21 | Agawam at Taconic | 07:00 PM | |
| co-ed Hockey | Jan 21 | McCann Tech at Brattleboro | Nelson Withington | 07:15 PM |
| co-ed Swimming | Jan 21 | Taconic Hills at Wahconah | YMCA | 04:30 PM |
| co-ed Swimming | Jan 21 | Mt. Anthony (VT) at Monument Mountain | Kilpatrick | 06:00 PM |
| Girls Basketball | Jan 21 | Taconic at Wahconah | 07:00 PM | |
| Girls Basketball | Jan 21 | Pittsfield at Frontier | 07:30 PM | |
| Boys Basketball | Jan 22 | Lee at Hoosac Valley | 07:00 PM | |
| co-ed Skiing | Jan 22 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Jan 22 | Springfield Central at Pittsfield | 06:00 PM | |
| Girls Basketball | Jan 22 | Westfield Tech at McCann Tech | 07:00 PM | |
| Girls Basketball | Jan 22 | Mount Greylock at Drury | 07:00 PM | |
| Girls Basketball | Jan 22 | Lenox at Lee | 07:00 PM | |
| Girls Basketball | Jan 22 | Hoosac Valley at Mt. Anthony | 07:00 PM | |
| Boys Basketball | Jan 23 | McCann Tech at Smith Voc. | 06:30 PM | |
| Boys Basketball | Jan 23 | Hampden Charter at Mount Everett | 06:30 PM | |
| Boys Basketball | Jan 23 | Lenox at Easthampton | 07:00 PM | |
| Boys Basketball | Jan 23 | Mount Greylock at Monument Mountain | 07:00 PM | |
| co-ed Bowling | Jan 23 | Multiple teams at Berkshire County League | Cove | 04:00 PM |
| co-ed Swimming | Jan 23 | Monument Mountain at Taconic | YMCA | 04:30 PM |
| co-ed Swimming | Jan 23 | Pittsfield at Mt. Anthony (VT) | Bennington Rec Center | 04:30 PM |
| Girls Basketball | Jan 23 | Mount Greylock at Lenox | 06:00 PM | |
| Girls Basketball | Jan 23 | Renaissance at Taconic | 06:00 PM | |
| Girls Basketball | Jan 23 | Lee at Mohawk | 07:00 PM | |
| Girls Basketball | Jan 23 | Wahconah at Pope Francis | 07:00 PM | |
| Girls Basketball | Jan 23 | Agawam at Drury | 07:00 PM | |
| co-ed Hockey | Jan 24 | McCann Tech at Easthampton | Lossone | 07:00 PM |
| co-ed Wrestling | Jan 24 | Mount Greylock at Otter Valley | 09:00 AM | |
| Boys Basketball | Jan 26 | Wahconah at Auburn | 06:00 PM | |
| Boys Basketball | Jan 26 | Smith Voc. at Lenox | 07:00 PM | |
| co-ed Swimming | Jan 26 | New Lebanon at Wahconah | YMCA | 04:30 PM |
| co-ed Swimming | Jan 26 | Monument Mountain at Pittsfield | 04:30 PM | |
| Girls Basketball | Jan 26 | McCann Tech at Commerce | 06:00 PM | |
| Girls Basketball | Jan 26 | Lee at Taconic | 06:00 PM | |
| Girls Basketball | Jan 26 | Gateway at Mount Everett | 06:30 PM | |
| Girls Basketball | Jan 26 | Pittsfield at Longmeadow | 07:00 PM | |
| Girls Basketball | Jan 26 | Pope Francis at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Jan 26 | Mount Greylock at Monument Mountain | 07:00 PM | |
| Boys Basketball | Jan 27 | Lenox at Libertas Academy Charter | 06:00 PM | |
| Boys Basketball | Jan 27 | Mount Everett at Lee | 06:30 PM | |
| Boys Basketball | Jan 27 | Mount Greylock at Veritas Prep | 07:00 PM | |
| Boys Basketball | Jan 27 | Hoosac Valley at Taconic | 07:00 PM | |
| Boys Basketball | Jan 27 | McCann Tech at Franklin Tech | 07:00 PM | |
| Boys Basketball | Jan 27 | Monument Mountain at Drury | 07:00 PM | |
| Girls Basketball | Jan 27 | Wahconah at Lenox | 06:00 PM | |
| Boys Basketball | Jan 28 | Pittsfield at Wahconah | 07:00 PM | |
| co-ed Bowling | Jan 28 | Multiple teams at Berkshire County League | Cove | 04:00 PM |
| co-ed Hockey | Jan 28 | Easthampton at Taconic | Boys and Girls Club | 07:15 PM |
| co-ed Skiing | Jan 28 | Multiple teams at Berkshire Nordic League | Mount Greylock | 03:00 PM |
| Girls Basketball | Jan 28 | Pioneer Valley at McCann Tech | 06:00 PM | |
| Boys Basketball | Jan 29 | Easthampton at Monument Mountain | 05:30 PM | |
| Boys Basketball | Jan 29 | Hoosac Valley at Pioneer Valley | 07:30 PM | |
| co-ed Hockey | Jan 29 | Taconic at Amherst | Amherst College | 08:30 PM |
| co-ed Skiing | Jan 29 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Jan 29 | Pioneer Valley CICS at McCann Tech | 06:00 PM | |
| Girls Basketball | Jan 29 | Hoosac Valley at Lenox | 06:00 PM | |
| Girls Basketball | Jan 29 | Taconic at Mount Greylock | 06:00 PM | |
| Girls Basketball | Jan 29 | Mount Everett at Hampden Charter | 06:00 PM | |
| Girls Basketball | Jan 29 | Pittsfield at Minnechaug | 06:30 PM | |
| Girls Basketball | Jan 29 | Easthampton at Monument Mountain | 07:00 PM | |
| Girls Basketball | Jan 29 | Frontier at Wahconah | 07:00 PM | |
| Girls Basketball | Jan 29 | Pope Francis at Drury | 07:00 PM | |
| Girls Basketball | Jan 29 | PVCS at Lee | 07:00 PM | |
| Boys Basketball | Jan 30 | Pioneer Valley Chinese Immersion at McCann Tech | 06:00 PM | |
| Boys Basketball | Jan 30 | Mount Everett at Libertas Academy Charter | 06:00 PM | |
| Boys Basketball | Jan 30 | Lenox at Veritas Prep | 06:30 PM | |
| Boys Basketball | Jan 30 | Taconic at Monument Mountain | 07:00 PM | |
| Boys Basketball | Jan 30 | Drury at Wahconah | 07:00 PM | |
| Boys Basketball | Jan 30 | Mount Greylock at Lee | 07:00 PM | |
| co-ed Bowling | Jan 30 | Multiple teams at Berkshire County League | King Pins (North Adams) | 04:00 PM |
| Boys Basketball | Feb 02 | Taconic at Sci-Tech | 07:00 PM | |
| Boys Basketball | Feb 02 | Northampton at Drury | 07:00 PM | |
| Boys Basketball | Feb 02 | McCann Tech at Mount Greylock | 07:00 PM | |
| Boys Basketball | Feb 02 | Hoosac Valley at Lee | 07:00 PM | |
| Boys Basketball | Feb 02 | Greenfield at Wahconah | 07:00 PM | |
| Girls Basketball | Feb 02 | St Mary’s at McCann Tech | 06:00 PM | |
| Girls Basketball | Feb 02 | Drury at Lenox | 06:00 PM | |
| Girls Basketball | Feb 02 | Northampton at Pittsfield | 06:00 PM | |
| Girls Basketball | Feb 02 | Mount Everett at Pioneer Valley CICS | 06:00 PM | |
| Girls Basketball | Feb 02 | Mount Greylock at Easthampton | 06:30 PM | |
| Girls Basketball | Feb 02 | Wahconah at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Feb 02 | Taconic at PVCS | Time TBA | 12:00 PM |
| Boys Basketball | Feb 03 | Mount Everett at Hampden Charter | 06:30 PM | |
| Boys Basketball | Feb 03 | Drury at Lenox | 07:00 PM | |
| Girls Basketball | Feb 03 | Monument Mountain at Lee | 07:00 PM | |
| Boys Basketball | Feb 04 | Pittsfield at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Feb 04 | Pittsfield at Wahconah | 06:00 PM | |
| Girls Basketball | Feb 04 | PVCS at Lenox | 06:00 PM | |
| Girls Basketball | Feb 04 | South Hadley at Drury | 07:00 PM | |
| Girls Basketball | Feb 04 | Belchertown at Monument Mountain | 07:00 PM | |
| Girls Basketball | Feb 04 | Hoosac Valley at Lee | 07:00 PM | |
| co-ed Hockey | Feb 05 | Taconic at Chicopee | Fitzpatrick | 05:30 PM |
| co-ed Skiing | Feb 05 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Feb 05 | Westfield Tech at Mount Everett | 06:30 PM | |
| Girls Basketball | Feb 05 | McCann Tech at Gateway | 06:30 PM | |
| Boys Basketball | Feb 06 | Mount Greylock at Mount Everett | 06:30 PM | |
| Boys Basketball | Feb 06 | Lee at Lenox | 07:00 PM | |
| Boys Basketball | Feb 06 | Wahconah at Monument Mountain | 07:00 PM | |
| Boys Basketball | Feb 06 | Taconic at Pittsfield | Boys and Girls Club | 07:00 PM |
| Boys Basketball | Feb 06 | Drury at Hoosac Valley | 07:00 PM | |
| Boys Basketball | Feb 06 | McCann Tech at Mohawk | 07:00 PM | |
| co-ed Bowling | Feb 06 | Multiple teams at Berkshire County League | K&M Bowling | 04:00 PM |
| Girls Basketball | Feb 06 | Taconic at Pittsfield | Boys and Girls Club | 05:30 PM |
| Girls Basketball | Feb 06 | Monson at Lee | 06:00 PM | |
| co-ed Hockey | Feb 07 | McCann Tech at Taconic | Boys and Girls Club | 07:15 PM |
| co-ed Skiing | Feb 07 | Multiple teams at Berkshire Nordic League | Mount Greylock | 10:00 AM |
| co-ed Wrestling | Feb 07 | Multiple teams at Berkshire County Duals | Mount Everett | 10:00 AM |
| Girls Basketball | Feb 07 | Wahconah at Taconic | 11:00 AM | |
| Boys Basketball | Feb 09 | Hoosac Valley at Veritas Prep | 06:30 PM | |
| Boys Basketball | Feb 09 | Belchertown at Monument Mountain | 07:00 PM | |
| Boys Basketball | Feb 09 | South Hadley at Wahconah | 07:00 PM | |
| Boys Basketball | Feb 09 | Pioneer Valley at Drury | 07:00 PM | |
| Boys Basketball | Feb 09 | Pittsfield at Northampton | 07:30 PM | |
| co-ed Skiing | Feb 09 | Multiple teams at Berkshire County Alpine League | Bousquet | 05:30 PM |
| Girls Basketball | Feb 09 | Wahconah at South Hadley | 07:00 PM | |
| Girls Basketball | Feb 09 | Drury at Frontier | 07:30 PM | |
| co-ed Skiing | Feb 10 | Multiple teams at State Nordic Meet | Prospect Mountain | 11:00 AM |
| co-ed Hockey | Feb 11 | Chicopee at Taconic | Boys and Girls Club | 07:15 PM |
| Girls Basketball | Feb 11 | Monument Mountain at Bay Path Voc. | 08:30 PM | |
| co-ed Bowling | Feb 13 | Multiple teams at Berkshire County Championship | Cove | 04:00 PM |
| Boys Basketball | Feb 14 | Classical at Taconic | 05:00 PM | |
| co-ed Skiing | Feb 24 | Multiple teams at State Alpine Ski Meet | TBA | 09:30 AM |
| co-ed Bowling | Feb 28 | Multiple teams at State Team Championship | Cove | 01:30 PM |
| co-ed Bowling | Mar 01 | Multiple teams at State Individual Championships | Time TBA, State Individual Chapionships | 12:00 AM |
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Drury High Celebrates Student-Athletes Headed to the Next Level
