SCHEDULE
| Sport | Date | Teams | Location | Time |
| Boys Basketball | Mar 04 | Monument Mountain at West Bridgewater | D4 State Tournament Round of 16 | 05:00 PM |
| Baseball | Mar 28 | Monument Mountain at Pittsfield | Clapp Park | 01:00 PM |
| Baseball | Mar 30 | Frontier at Monument Mountain | 04:30 PM | |
| Softball | Apr 02 | Lenox at Monument Mountain | 04:30 PM | |
| Baseball | Apr 03 | Hopkins at Monument Mountain | 04:30 PM | |
| Softball | Apr 03 | Westfield at Monument Mountain | 04:30 PM | |
| Baseball | Apr 06 | Monument Mountain at Ware | St. Joseph's Field, Palmer | 07:00 PM |
| Softball | Apr 06 | Monument Mountain at Wahconah | Pine Grove Park | 04:30 PM |
| Baseball | Apr 09 | Monument Mountain at Drury | Joe Wolfe | 04:00 PM |
| Softball | Apr 09 | Monument Mountain at Mount Greylock | 04:15 PM | |
| Baseball | Apr 11 | Taconic at Monument Mountain | 01:00 PM | |
| Softball | Apr 13 | Monument Mountain at Taconic | 04:30 PM | |
| Baseball | Apr 14 | Hampshire at Monument Mountain | 04:30 PM | |
| Baseball | Apr 16 | Monument Mountain at Lenox | War Memorial Field | 04:00 PM |
| Softball | Apr 16 | Hoosac Valley at Monument Mountain | 04:30 PM | |
| Baseball | Apr 18 | Monument Mountain at Wahconah | 01:00 PM | |
| Softball | Apr 18 | Pittsfield at Monument Mountain | 01:00 PM | |
| Softball | Apr 21 | Monument Mountain at Lenox | 04:30 PM | |
| Baseball | Apr 22 | Southwick at Monument Mountain | 04:30 PM | |
| Baseball | Apr 24 | Ware at Monument Mountain | 04:30 PM | |
| Softball | Apr 25 | Monument Mountain at Drury | Alcombright | 11:00 AM |
| Baseball | Apr 27 | Drury at Monument Mountain | 04:30 PM | |
| Softball | Apr 29 | Wahconah at Monument Mountain | 04:30 PM | |
| Baseball | Apr 30 | Monument Mountain at Hampshire | 04:00 PM | |
| Softball | May 01 | Mount Greylock at Monument Mountain | 04:30 PM | |
| Baseball | May 02 | Mount Greylock at Monument Mountain | 04:30 PM | |
| Softball | May 05 | Taconic at Monument Mountain | 04:30 PM | |
| Baseball | May 06 | Wahconah at Monument Mountain | 04:30 PM | |
| Baseball | May 08 | Monument Mountain at Southwick | 04:00 PM | |
| Softball | May 08 | Monument Mountain at Hoosac Valley | Russell Field | 04:00 PM |
| Baseball | May 11 | Monument Mountain at Northampton | 04:45 PM | |
| Softball | May 12 | Monument Mountain at Housatonic Valley | 04:30 PM | |
| Baseball | May 13 | Monument Mountain at Belchertown | 04:00 PM | |
| Softball | May 14 | Westfield Tech at Monument Mountain | 05:30 PM | |
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Summers Sinks 3 in Pittsfield Tourney Win
