SCHEDULE
| Sport | Date | Teams | Location | Time |
| Boys Basketball | Oct 07 | Pittsfield at Mount Greylock Unified | 04:00 PM | |
| Boys Soccer | Oct 07 | Pittsfield at Mount Greylock | 06:00 PM | |
| Volleyball | Oct 07 | Taconic at Pittsfield | 06:00 PM | |
| Girls Soccer | Oct 08 | Pittsfield at Chicopee Comp | 07:00 PM | |
| Boys Soccer | Oct 09 | Pittsfield at Westfield | 04:00 PM | |
| Volleyball | Oct 09 | Pittsfield at Wahconah | 06:15 PM | |
| Girls Soccer | Oct 10 | Agawam at Pittsfield | Kirvin Park | 04:00 PM |
| Boys Soccer | Oct 11 | Pittsfield at Hampshire | 07:00 PM | |
| Football | Oct 11 | Pittsfield at Chicopee | 06:00 PM | |
| Volleyball | Oct 11 | Pittsfield at West Springfield | 05:30 PM | |
| Boys Soccer | Oct 14 | Mount Greylock at Pittsfield | Kirvin Park | 04:30 PM |
| Girls Soccer | Oct 14 | Pittsfield at Wahconah | 07:00 PM | |
| Volleyball | Oct 14 | Pittsfield at Taconic | 06:00 PM | |
| Boys Soccer | Oct 16 | Pope Francis at Pittsfield | Kirvin Park | 04:00 PM |
| Volleyball | Oct 16 | Lee at Pittsfield | 06:00 PM | |
| Boys Soccer | Oct 18 | Minnechaug at Pittsfield | Kirvin Park | 04:00 PM |
| Football | Oct 18 | Ludlow at Pittsfield | 07:00 PM | |
| Volleyball | Oct 18 | Pittsfield at Agawam | 06:00 PM | |
| Football | Oct 25 | Pittsfield at Taconic | 04:30 PM | |
| Boys Basketball | Oct 29 | Pittsfield at Westfield Unified | 03:30 PM | |
| Football | Nov 02 | Putnam Voc at Pittsfield | 07:00 PM | |
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Stringer Scores Game-Winner as Wahconah Tops Lenox
