The Sachems' Caleb Unni knocked down a three-pointer with 14 seconds left to give Winchester the lead.
Former Coach Paul Sobolewski resigned and the school hopes to hire a new coach by the end of March.
Nick Cashion and Ryan MacDonald both qualified through the consolation rounds.
Here's a look back at the week in Winchester sports.
Take a look back at the week in Winchester sports.
Despite graduating six of its top seven wrestlers a year ago, the Sachems continue to dominate the Middlesex League.
After losing to Burlington earlier in the season, the Sachems won the second contest, 3-0.
The boys came back to win in overtime, while the girls controlled the tempo as they defeated the Warriors.
Senior Michaela Chiuccariello scored five goals leading Winchester to its first win of the season, 6-1 over Belmont.
The Sachems failed to meet their coach's expectations at the Sons of Italy Tournament on Saturday.
The Winchester girl's hockey team started the season with a 0-0 draw against Reading.
The two longtime rivals will meet for the 106th time Thursday at 10:15 a.m. at Woburn High School.
After defeating Stoneham 2-0, the Winchester field hockey team has started the season 2-0.
Winchester hosts Cal Ripken Regional Tournament and Pop Warner starts its first season in 30 years.
On September 21, the Sachem Youth Football and Cheerleading Program will be hosting Melrose on its brand new stadium, while the cover-band Ernie and the Automatics perform during halftime.