| Sport | Date | Teams | Location | Time |
| Baseball | May 23 | Belchertown at Pittsfield | WMass Class B quarter-final | 04:00 PM |
| Baseball | May 23 | Smith Voc. at McCann Tech | Joe Wolfe WMass Class C quarter-final | 04:00 PM |
| Baseball | May 23 | Wahconah at Monument Mountain | WMass Class B quarter-final | 04:30 PM |
| Baseball | May 23 | Franklin Tech at Mount Greylock | WMass Class C quarter-final | 04:30 PM |
| Baseball | May 23 | Hampshire at Taconic | WMass Class B quarter-final | 04:30 PM |
| Baseball | May 23 | Lenox at Greenfield | WMass Class C quarter-final | 06:00 PM |
| Boys Lacrosse | May 23 | Lenox at Hoosac Valley | | 04:30 PM |
| Boys Lacrosse | May 23 | St Mary’s at McCann Tech | | 04:30 PM |
| Girls Lacrosse | May 23 | Northampton at Mount Greylock | | 06:00 PM |
| Softball | May 23 | Athol at Taconic | WMass Class C quarter-final | 04:30 PM |
| Softball | May 23 | Southwick at Pittsfield | WMass Class B quarter-final | 04:30 PM |
| Softball | May 23 | St Mary’s at Mount Everett | | 04:30 PM |
| Softball | May 23 | Drury at Mount Greylock | WMass Class C quarter-final | 04:30 PM |
| Softball | May 23 | Monument Mountain at Hampshire | WMass Class B quarter-final | 05:00 PM |
| Softball | May 23 | Lenox at Palmer | | 06:00 PM |
| |
| Baseball | May 24 | Smith Academy at Mount Everett | WMass Class D quarter-final | 04:00 PM |
| Baseball | May 24 | Mahar at Hoosac Valley | | 04:30 PM |
| Boys Lacrosse | May 24 | Pittsfield at Smith Voc. | | 04:00 PM |
| Boys Lacrosse | May 24 | McCann Tech at Monson | | 04:00 PM |
| Boys Lacrosse | May 24 | Hoosac Valley at St Mary’s | | 04:00 PM |
| Softball | May 24 | Lee at Hopkins | WMass Class D quarter-final | 04:00 PM |
| Softball | May 24 | Ware at Hoosac Valley | WMass Class D quarter-final | 04:30 PM |
| Softball | May 24 | Chicopee at Wahconah | WMass Class B quarter-final | 06:00 PM |
| |
| Baseball | May 25 | Athol at Drury | | 04:00 PM |
| Boys Lacrosse | May 25 | St Mary’s at Lenox | | 05:00 PM |
| Boys Lacrosse | May 25 | Northampton at Wahconah | | 05:30 PM |
| co-ed Track & Field | May 25 | Wahconah at Unified State Championship | Natick HS | 10:00 AM |
| Girls Lacrosse | May 25 | Hoosac Valley at Hampshire | | 03:00 PM |
| Girls Lacrosse | May 25 | Chic Comp at Mount Greylock | | 06:00 PM |
| Girls Lacrosse | May 25 | Wahconah at Northampton | | 07:00 PM |
| Softball | May 25 | Ware at Hoosac Valley | Russell Field, regular season game | 04:30 PM |
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| Baseball | May 26 | Hoosac Valley at Science and Technology | | 04:30 PM |
| Boys Lacrosse | May 26 | St Mary’s at Pittsfield | Egremont Elementary | 04:30 PM |
| co-ed Track & Field | May 26 | Mount Greylock at MIAA Division 6 Meet | Westfield State | 03:00 PM |
| co-ed Track & Field | May 26 | Monument Mountain at MIAA Division 6 Meet | Westfield State | 03:00 PM |
| co-ed Track & Field | May 26 | Lenox at MIAA Division 5 Meet | Weston High School | 03:00 PM |
| co-ed Track & Field | May 26 | Taconic at MIAA Division 6 Meet | Westfield State | 03:00 PM |
| co-ed Track & Field | May 26 | Pittsfield at MIAA Division 5 Meet | Weston High School | 03:00 PM |
| co-ed Track & Field | May 26 | Hoosac Valley at MIAA Division 6 Meet | Westfield State | 03:00 PM |
| co-ed Track & Field | May 26 | Wahconah at MIAA Division 6 Meet | Westfield State | 03:00 PM |
| Girls Lacrosse | May 26 | Hampshire at Lee | | 04:00 PM |
| Girls Lacrosse | May 26 | Wahconah at Mount Greylock | | 06:00 PM |
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| Baseball | May 27 | Drury at Ludlow | | 04:00 PM |
| Girls Lacrosse | May 27 | Belchertown at Mount Greylock | | 05:30 PM |
| |
| co-ed Track & Field | May 28 | Hoosac Valley at MIAA Division 6 Meet | Westfield State | 02:30 PM |
| co-ed Track & Field | May 28 | Wahconah at MIAA Division 6 Meet | Westfield State | 02:30 PM |
| co-ed Track & Field | May 28 | Pittsfield at MIAA Division 5 Meet | Weston High School | 02:30 PM |
| co-ed Track & Field | May 28 | Mount Greylock at MIAA Division 6 Meet | Westfield State | 02:30 PM |
| co-ed Track & Field | May 28 | Monument Mountain at MIAA Division 6 Meet | Westfield State | 02:30 PM |
| co-ed Track & Field | May 28 | Taconic at MIAA Division 6 Meet | Westfield State | 02:30 PM |
| co-ed Track & Field | May 28 | Lenox at MIAA Division 5 Meet | Weston High School | 02:30 PM |
