- Mar 17 - Berkshire County Basketball All-Stars Meet at Boys and Girls Club
Pittsfield High’s Da’Sean Brown hit his second half-court shot of the fourth quarter Friday to cap a 108-83 win for the South All-Stars in the Berkshire County Basketball Officials All-Star Game at the Boys and Girls Club.
- Mar 07 - Bishop Stang Pulls Away from Pittsfield in Fourth Quarter
The Bishop Stang boys basketball team used an 8-0 fourth-quarter run to take the lead for good in a back-and-forth game and came away with a 71-65 win over Pittsfield on Tuesday in the Division 3 State Tournament Sweet 16.
- Mar 02 - Shepardson, Mungin Lead Generals in Tourney Opener
Makai Shepardson scored a game-high 21 points, and Carter Mungin had a double-double with 19 points and 12 rebounds as Pittsfield improved to 17-4 and earned a home game in the Sweet 16 against the winner of Friday’s game between No. 12 Hudson and No. 21 Bishop Stang.
- Feb 22 - Pittsfield Boys Bounce Back with Win over Wahconah
Da'Sean Brown scored 21 points Wednesday to lead the Pittsfield boys basketball team to a 77-64 win over Wahconah in the regular season finale for both teams.
- Feb 20 - South Hadley Edges Pittsfield Boys in Regional Quarter-Finals
Colin Quinn scored 21 points, and the South Hadley boys basketball team Monday held off a comeback bid by Pittsfield in the quarter-finals of the Western Massachusetts Class B tournament.
- Feb 15 - Brown Leads Pittsfield to Victory in Regular Season Finale
Da’Sean Brown scored 20 points Wednesday to lead the Pittsfield boys basketball team to a 70-59 win over East Longmeadow.
- Feb 11 - Brown Leads Generals Past Agawam
Da’Sean Brown scored 25 points, and the Pittsfield boys basketball team broke open a close game in the second half to take a 78-59 win over Agawam on Saturday.
- Feb 10 - Arce-Jackson Leads Generals Past West Springfield
Keanu Arce-Jackson scored 19 points Friday to lead the Pittsfield boys basketball team to a 52-37 win over West Springfield.
- Feb 07 - Pittsfield Tops Minnechaug on Senior Night
Makai Shepardson and Keanu Arce-Jackson each scored 17 points, and the Pittsfield boys basketball team Tuesday outscored Minnechaug down the stretch to take a 65-63 win.
- Jan 30 - Brennan Helps Generals Top Wahconah in OT
Patrick Brennan scored six points in overtime to help the Pittsfield boys basketball team earn a 71-8 win over Wahconah on Monday night.
- Jan 27 - Arce-Jackson, Shepardson Lead Generals Past Colts
Keanu Arce-Jackson and Makai Shepardson Friday led the Pittsfield boys basketball team to a 70-63 win over Chicopee Comprehensive.
- Jan 24 - West Side Pulls Away Late, Snaps Pittsfield Win Streak
Joseph Ingegneri scored 27 points, and the West Springfield boys basketball team Tuesday pulled away in the fourth quarter to earn a 77-70 win over Pittsfield in a battle for first place in the Suburban North.
- Jan 21 - Brown, Generals Top Minnechaug
Da'Sean Brown scored 22 points to lead four Pittsfield players in double figures as the Generals edged Minnechaug, 73-71, on Saturday.
- Jan 18 - Pittsfield Boys Knock Off Monument Mountain
Makai Shepardson tied for game-high scoring honors with 23 points, and Da’Sean Brown and Carter Mungin added 18 and 17, respectively.
- Jan 12 - Shepardson, Generals Jump Ahead Early in Winning Sixth Straight
Makai Shepardson scored 10 points in a big first quarter for the Pittsfield boys basketball team, which went on to a 69-49 win over Agawam on Thursday night.
- Jan 09 - Pittsfield Ends Drought Against Taconic
After six long years and 14 losses, Pittsfield Monday earned a 67-52 win over Taconic at the Boys and Girls Club.
- Jan 03 - Brown Scores 30 as Generals Stay Hot
Da’Sean Brown scored 30 points Tuesday to lead the Pittsfield boys basketball team to an 88-67 win over Mount Anthony.
- Dec 30 - Pittsfield Drops Amherst for Third Straight Win
Pittsfield forced 18 turnovers and blocked six shots in a 50-37 win over Amherst that capped a 3-0 holiday week for coach Jerome Edgerton's team.
- Dec 28 - Brown Helps Key Second-Half Comeback for Generals
Carter Mungin scored 21 points, and Da’Sean Brown sparked a second half comeback as the Pittsfield boys basketball team beat Guilderland, 57-47, on Wednesday night.
- Dec 27 - Pittsfield Boys Beat Colonie, N.Y., in Overtime
Carter Mungin scored 20 points Tuesday to lead the Pittsfield boys basketball team to a 65-62, overtime win over Colonie High School.
- Dec 22 - Pittsfield Boys Fall at Pope Francis
Ryan Vedovelli scored 21 points Thursday to lead the Pope Francis boys basketball team to a 70-56 win over Pittsfield.
- Dec 19 - Mungin Leads Generals to Road Win
Carter Mungin scored 16 points Monday to lead the Pittsfield boys basketball team to a 77-64 win over Westfield.
- Dec 13 - Taconic Takes Control in Second Half of Win Over Pittsfield
Christian Maturevich scored 20 points, and Tayvon Sandifer added 15 as Taconic defeated Pittsfield, 79-58, to improve to 2-0 this season.