• Oct 31 - Pittsfield Takes First Loss in Shootout with Putnam
  The Putnam Voc football team Thursday rallied from an 18-point second-half deficit to earn a 52-50 win over Pittsfield in the regular season finale for both teams.
• Oct 25 - Pittsfield Runs Past Taconic to Stay Unbeaten
  The Pittsfield High football team grabbed bragging rights with a 48-0 win over city rival Taconic on Friday at Berkshire Community College.
• Oct 18 - Jubrey Leads Pittsfield to 6-0 Mark
  Marcus Jubrey proved to be too much to handle for Ludlow's defense, throwing two touchdowns and rushing for four. Jubrey led the team in rushing yards with more than 280 yards on the ground, three of which came in the first half.
• Sep 27 - Pittsfield Wins Big over Wahconah
  Both running back Elias Robinson and quarterback Marcus Jubrey had monster nights for the Generals, scoring a combined seven touchdowns and over 100 yards rushing for each. Two of their touchdowns came through the air with a 33-yard score and a 49-yard score.
• Sep 19 - Jubrey, Generals Bludgeon Belchertown
  Marcus Jubrey ran for 123 yards and three touchdowns and threw for another touchdown.