| Sport | Date | Teams | Location | Time |
| Girls Basketball | Feb 27 | Quabbin at Taconic | WMass D3 quarter-finals | 06:00 PM |
| Girls Basketball | Feb 27 | Frontier at Wahconah | WMass D3 quarter-finals | 07:00 PM |
| Girls Basketball | Feb 27 | Franklin Tech at Lee | WMass D4 quarter-final | 07:00 PM |
| Girls Basketball | Feb 27 | Granby at Hoosac Valley | WMass D3 quarter-finals | 07:00 PM |
| Girls Basketball | Feb 27 | Hopkins Academy at Lenox | WMass D4 quarter-final | 07:00 PM |
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| Boys Basketball | Feb 28 | Belchertown at Taconic | WMass D2 quarter-finals | 07:00 PM |
| Boys Basketball | Feb 28 | Mount Greylock at Narragansett | WMass D3 quarter-finals | 07:00 PM |
| Boys Basketball | Feb 28 | Turners Falls at Drury | WMass D4 quarter-final | 07:00 PM |
| Boys Basketball | Feb 28 | Murdock at Wahconah | WMass D3 quarter-finals | 07:00 PM |
| Boys Basketball | Feb 28 | Lenox at Monson | WMass D4 quarter-final | 07:00 PM |
| Boys Basketball | Feb 28 | Monument Mountain at Frontier | WMass D3 quarter-finals | 07:00 PM |
| co-ed Bowling | Feb 28 | Multiple teams at Berkshire County Championship | Ken's | 04:00 PM |
| co-ed Wrestling | Feb 28 | Multiple teams at All-State Meet | Methuen High School | 10:00 AM |
| Girls Basketball | Feb 28 | Pittsfield at Northampton | WMass D2 quarter-finals | 07:00 PM |
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| co-ed Hockey | Feb 29 | Wahconah at Amherst | Olympia, WMass D3A semi-final | 04:00 PM |
| co-ed Wrestling | Feb 29 | Multiple teams at All-State Meet | Methuen High School | 10:00 AM |
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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 |
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| Girls Lacrosse | Apr 02 | Mount Greylock at Granby | | 04:00 PM |
| Softball | Apr 02 | Mount Greylock at Wahconah | | 04:00 PM |
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| Baseball | Apr 04 | Mount Greylock at Lenox | | 03:30 PM |
| Boys Lacrosse | Apr 04 | Mount Greylock at Tantasqua | | 11:00 AM |
| Girls Lacrosse | Apr 04 | Mount Greylock at West Springfield | | 01:00 PM |
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| Softball | Apr 07 | Lenox at Mount Greylock | | 04:30 PM |
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| Girls Lacrosse | Apr 09 | Mount Greylock at Lee | | 04:30 PM |
| Softball | Apr 09 | Mount Greylock at McCann Tech | | 04:15 PM |
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| Baseball | Apr 10 | Mount Greylock at Mount Everett | | 04:30 PM |
| Boys Lacrosse | Apr 10 | Mount Greylock at Pittsfield | | 04:30 PM |
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| Softball | Apr 11 | Mount Greylock at Frontier | | 11:30 AM |
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| Baseball | Apr 13 | Taconic at Mount Greylock | | 04:00 PM |
| Boys Lacrosse | Apr 13 | Mt. Anthony (VT) at Mount Greylock | | 04:30 PM |
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| Girls Lacrosse | Apr 14 | Mount Greylock at Mt. Anthony (VT) | | 04:30 PM |
| Softball | Apr 14 | Pittsfield at Mount Greylock | | 04:30 PM |
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| Baseball | Apr 15 | Mount Greylock at Mt. Anthony (VT) | | 04:30 PM |
| Boys Lacrosse | Apr 15 | Lee at Mount Greylock | | 04:30 PM |
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| Girls Lacrosse | Apr 16 | Pittsfield at Mount Greylock | | 04:30 PM |
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| Boys Lacrosse | Apr 17 | Pope Francis at Mount Greylock | | 06:00 PM |
| Softball | Apr 17 | Mount Greylock at Mount Everett | | 04:30 PM |
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| Baseball | Apr 18 | Pittsfield at Mount Greylock | | 03:00 PM |
| Softball | Apr 18 | Monument Mountain at Mount Greylock | | 01:00 PM |
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| Baseball | Apr 20 | Mount Greylock at Hoosac Valley | | 01:00 PM |
| Boys Lacrosse | Apr 20 | Mount Greylock at Wahconah | | 04:30 PM |
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| Girls Lacrosse | Apr 21 | Mount Greylock at Hoosac Valley | | 04:30 PM |
| Softball | Apr 21 | Drury at Mount Greylock | | 04:00 PM |
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| Baseball | Apr 22 | Wahconah at Mount Greylock | | 03:00 PM |
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| Softball | Apr 23 | Mount Greylock at Hoosac Valley | | 04:30 PM |
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| Baseball | Apr 24 | Lee at Mount Greylock | | 03:00 PM |
| Girls Lacrosse | Apr 24 | E. Longmeadow at Mount Greylock | | 06:00 PM |
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| Baseball | Apr 27 | Mount Greylock at Taconic | | 04:30 PM |
| Boys Lacrosse | Apr 27 | Hoosac Valley at Mount Greylock | | 04:30 PM |
| Softball | Apr 27 | Paolo Freire Charter at Mount Greylock | | 04:30 PM |
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| Girls Lacrosse | Apr 28 | Wahconah at Mount Greylock | | 06:00 PM |
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| Baseball | Apr 29 | Mount Everett at Mount Greylock | | 04:30 PM |
| Boys Lacrosse | Apr 29 | Mount Greylock at Northampton | | 05:00 PM |
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| Baseball | Apr 30 | Monument Mountain at Mount Greylock | | 04:30 PM |
| Girls Lacrosse | Apr 30 | Mount Greylock at Burr and Burton | | 04:30 PM |
| Softball | Apr 30 | Mount Greylock at Taconic | | 04:30 PM |
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| Boys Lacrosse | May 01 | Mount Greylock at Mt. Anthony (VT) | | 04:30 PM |
| Softball | May 01 | Hoosac Valley at Mount Greylock | | 04:15 PM |
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| Girls Lacrosse | May 04 | Mt. Anthony (VT) at Mount Greylock | | 04:30 PM |
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| Baseball | May 05 | Mount Greylock at Pittsfield | | 05:00 PM |
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| Girls Lacrosse | May 06 | Lee at Mount Greylock | | 04:30 PM |
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| Baseball | May 07 | Lenox at Mount Greylock | | 05:00 PM |
| Boys Lacrosse | May 07 | Burr and Burton at Mount Greylock | | 04:30 PM |
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| Girls Lacrosse | May 08 | S. Hadley at Mount Greylock | | 06:00 PM |
| Softball | May 08 | Mount Greylock at Hampden Charter | | 04:30 PM |
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| Baseball | May 09 | Mount Greylock at Wahconah | | 03:15 PM |
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| Baseball | May 11 | Mount Greylock at Monument Mountain | | 05:00 PM |
| Girls Lacrosse | May 11 | Mount Greylock at Pittsfield | | 04:30 PM |
| Softball | May 11 | Mount Everett at Mount Greylock | | 05:00 PM |
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| Boys Lacrosse | May 12 | Pittsfield at Mount Greylock | | 04:30 PM |
| Softball | May 12 | Mount Greylock at Drury | | 05:00 PM |
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| Boys Lacrosse | May 14 | Mount Greylock at Lee | | 04:30 PM |
| Softball | May 14 | Mount Greylock at Monument Mountain | | 05:00 PM |
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| Baseball | May 15 | Drury at Mount Greylock | | 05:00 PM |
| Girls Lacrosse | May 15 | Hoosac Valley at Mount Greylock | | 06:00 PM |
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| Baseball | May 18 | McCann Tech at Mount Greylock | | 04:00 PM |
| Girls Lacrosse | May 18 | Mount Greylock at Wahconah | | 06:00 PM |
| Softball | May 18 | Mount Greylock at Pittsfield | | 04:30 PM |
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| Baseball | May 19 | Hoosac Valley at Mount Greylock | | 04:30 PM |
| Boys Lacrosse | May 19 | Wahconah at Mount Greylock | | 04:30 PM |
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| Girls Lacrosse | May 20 | Mount Greylock at Chic Comp | | 04:30 PM |
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| Boys Lacrosse | May 21 | Mount Greylock at Hoosac Valley | | 04:30 PM |
| Softball | May 21 | Lee at Mount Greylock | | 04:30 PM |
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| Baseball | May 22 | Amherst at Mount Greylock | | 05:00 PM |
| Girls Lacrosse | May 22 | Westfield at Mount Greylock | | 06:00 PM |
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| Girls Lacrosse | May 25 | Northampton at Mount Greylock | | 04:30 PM |
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| Baseball | May 26 | Mount Greylock at Drury | | 04:30 PM |
| Softball | May 26 | Taconic at Mount Greylock | | 04:30 PM |
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| Softball | May 28 | Wahconah at Mount Greylock | | 04:15 PM |
