| Sport | Date | Teams | Location | Time |
| Girls Basketball | Dec 12 | Mount Greylock at Taconic | | 07:00 PM |
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| Boys Basketball | Dec 13 | Taconic at St. John Shrewsbury | | 07:00 PM |
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| Boys Basketball | Dec 15 | Putnam at Taconic | Curry Hicks Cage | 11:00 AM |
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| Girls Basketball | Dec 16 | Taconic at Hoosac Valley | | 01:00 PM |
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| Boys Basketball | Dec 17 | Longmeadow at Taconic | | 07:00 PM |
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| Girls Basketball | Dec 18 | Taconic at Pittsfield | | 07:00 PM |
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| Boys Basketball | Dec 19 | Green Tech at Taconic | B & G club | 07:30 PM |
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| Boys Basketball | Dec 23 | Taconic at Lenox | | 07:00 PM |
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| Boys Basketball | Dec 27 | Taconic at Cambridge Rindge | Cathedral High | 01:30 PM |
| Girls Basketball | Dec 27 | Lenox at Taconic | | 07:00 PM |
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| Boys Basketball | Dec 28 | Taconic at Acton Boxborough | Cathedral High | 11:55 AM |
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| Girls Basketball | Dec 30 | Taconic at Mount Everett | | 07:00 PM |
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| Girls Basketball | Jan 02 | Taconic at Belchertown | | 07:00 PM |
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| Boys Basketball | Jan 04 | Hamden at Taconic | | 02:00 PM |
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| Boys Basketball | Jan 06 | Taconic at Monument Mountain | | 07:00 PM |
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| Girls Basketball | Jan 07 | Taconic at Lee | | 07:00 PM |
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| Boys Basketball | Jan 08 | Pittsfield at Taconic | | 07:00 PM |
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| Boys Basketball | Jan 10 | Taconic at Wahconah | | 07:30 PM |
| Girls Basketball | Jan 10 | Taconic at Drury | | 07:00 PM |
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| Boys Basketball | Jan 13 | Drury at Taconic | | 07:00 PM |
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| Girls Basketball | Jan 15 | Taconic at Wahconah | | 07:00 PM |
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| Boys Basketball | Jan 16 | Chicopee at Taconic | Springfield College | 05:30 PM |
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| Girls Basketball | Jan 17 | West Springfield at Taconic | Springfield College | 04:00 PM |
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| Boys Basketball | Jan 21 | Taconic at Mount Greylock | | 07:00 PM |
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| Boys Basketball | Jan 24 | Pope Francis at Taconic | | 07:00 PM |
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| Girls Basketball | Jan 27 | Monument Mountain at Taconic | | 07:00 PM |
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| Boys Basketball | Jan 28 | Taconic at Drury | | 07:00 PM |
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| Boys Basketball | Jan 30 | Wahconah at Taconic | | 06:30 PM |
| Girls Basketball | Jan 30 | Wahconah at Taconic | | 08:00 PM |
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| Girls Basketball | Feb 03 | Hoosac Valley at Taconic | | 07:00 PM |
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| Boys Basketball | Feb 07 | Taconic at Pittsfield | B & G club | 07:00 PM |
| Girls Basketball | Feb 07 | Taconic at Pittsfield | B & G club | 05:30 PM |
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| Boys Basketball | Feb 10 | Hoosac Valley at Taconic | | 07:00 PM |
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| Girls Basketball | Feb 11 | E. Longmeadow at Taconic | | 06:00 PM |
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| Girls Basketball | Feb 13 | Greenfield at Taconic | | 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 |
| Girls Basketball | Feb 17 | TBA at Taconic | Wachusett | 03:20 AM |
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| Girls Basketball | Feb 19 | Taconic at Monument Mountain | | 07:00 PM |
