Red & Black Advance in Playoffs After Dramatic Overtime Win Against Andover

Author: Tommy Kowalczuk, WHS Class of '26

The Winchester boys varsity soccer team continued their postseason run with a thrilling 1-0 overtime victory over Andover in the third round of the state tournament. In a game defined by grit, defense, and heart, the Red & Black battled through two scoreless halves before breaking through in dramatic fashion during the second overtime period.

Injury timeout during action between Winchester and Andover Boys playoff soccer

Both teams came out strong, trading possession and chances early on, but neither could find the back of the net. The match was tight throughout regulation, with Winchester controlling much of the play and keeping Andover pinned in their own half for long stretches. Despite generating several quality scoring opportunities, the Red & Black were repeatedly denied by Andover’s outstanding goalkeeper, who made multiple crucial saves to keep his team alive.

As the first overtime ended still scoreless, Winchester entered the second extra period determined to finish the job. With just eight minutes left, senior Adam O’Riordan delivered a perfectly placed corner kick, setting up fellow senior Ean Errico, who rose above the defense and buried a header into the back of the net — sending the Winchester sideline and fans into celebration.

The goal capped off a commanding performance from the team’s defense, led by captains Marvin Li and Casey Trumbower, who anchored the back line and shut down Andover’s attack. Their composure and physicality kept the opposition’s offense contained for nearly the entire match.

Winchester also dominated the midfield for much of the night, maintaining possession and dictating the tempo. However, the victory came with concern, as midfielder Cole Queenan was helped off the field following an apparent injury. The team and fans are hopeful he’ll recover in time for the next round.

With the win, Winchester punches their ticket to the next round of the state tournament, carrying momentum, determination, and belief that this playoff run is far from over.