SCHEDULE
| Sport | Date | Teams | Location | Time |
| Boys Basketball | Dec 15 | Pittsfield at Drury | 07:00 PM | |
| Boys Basketball | Dec 19 | Pittsfield at Monument Mountain | 07:00 PM | |
| Girls Basketball | Dec 19 | South Hadley at Pittsfield | 06:00 PM | |
| Boys Basketball | Dec 22 | Wahconah at Pittsfield | 07:00 PM | |
| Boys Basketball | Dec 22 | Wahconah at Pittsfield | 07:00 PM | |
| Boys Basketball | Dec 27 | Springfield ICS at Pittsfield | 01:00 PM | |
| Girls Basketball | Dec 28 | Pittsfield at Hornell School | 08:30 PM | |
| Girls Basketball | Dec 29 | Pittsfield at Niskayuna | 05:30 PM | |
| Girls Basketball | Dec 30 | Longmeadow at Pittsfield | 06:00 PM | |
| Boys Basketball | Jan 02 | Pittsfield at Agawam | 07:00 PM | |
| Girls Basketball | Jan 02 | Drury at Pittsfield | 06:00 PM | |
| Boys Basketball | Jan 05 | Hoosac Valley at Pittsfield | 07:00 PM | |
| Girls Basketball | Jan 06 | Minnechaug at Pittsfield | 06:00 PM | |
| Boys Basketball | Jan 08 | Pittsfield at Taconic | Boys and Girls Club | 07:00 PM |
| Girls Basketball | Jan 08 | Pittsfield at Northampton | 07:30 PM | |
| Boys Basketball | Jan 12 | Belchertown at Pittsfield | 07:00 PM | |
| Boys Basketball | Jan 13 | Drury at Pittsfield | 07:00 PM | |
| Girls Basketball | Jan 13 | Pittsfield at Springfield Central | 07:00 PM | |
| Boys Basketball | Jan 15 | Monument Mountain at Pittsfield | 07:00 PM | |
| Girls Basketball | Jan 15 | Pittsfield at South Hadley | 07:00 PM | |
| Boys Basketball | Jan 17 | Niskayuna at Pittsfield | Springfield Central, Hoophall | 11:45 AM |
| 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 |
| Girls Basketball | Jan 18 | Pittsfield at TBA | Time TBA, Springfield Central, Hoophall | 12:00 PM |
| Boys Basketball | Jan 20 | Pittsfield at Holyoke | 07:00 PM | |
| Girls Basketball | Jan 21 | Pittsfield at Frontier | 07:30 PM | |
| Girls Basketball | Jan 22 | Springfield Central at Pittsfield | 06:00 PM | |
| Girls Basketball | Jan 26 | Pittsfield at Longmeadow | 07:00 PM | |
| Boys Basketball | Jan 28 | Pittsfield at Wahconah | 07:00 PM | |
| Girls Basketball | Jan 29 | Pittsfield at Minnechaug | 06:30 PM | |
| Girls Basketball | Feb 02 | Northampton at Pittsfield | 06:00 PM | |
| Boys Basketball | Feb 04 | Pittsfield at Hoosac Valley | 07:00 PM | |
| Girls Basketball | Feb 04 | Pittsfield at Wahconah | 06:00 PM | |
| Boys Basketball | Feb 06 | Taconic at Pittsfield | Boys and Girls Club | 07:00 PM |
| Girls Basketball | Feb 06 | Taconic at Pittsfield | Boys and Girls Club | 05:30 PM |
| Boys Basketball | Feb 09 | Pittsfield at Northampton | 07:30 PM | |
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Drury High Celebrates Student-Athletes Headed to the Next Level
