DORCHESTER >> After two close losses to Boston College High in the regular season and three last year, Carl Stredicke decided enough was enough.

It was time for the Winchester boys tennis team to finally take down the Eagles.

Stredicke’s quick win at No. 2 singles set the stage for the No. 10 Red and Black, who upset the No. 7 Eagles 3-2 in the Division 1 tennis tournament’s Round of 16 at BC High.

Winchester (17-4), which is going for its first state title since 2018, will face either No. 2 Acton-Boxboro or No. 18 Andover, who played Thursday evening, in the state quarterfinals.

“When you lose five times in a row to a team, you’re not really afraid of them any more,” said Winchester coach Mike Lauretano. “This time going into it, they were hungry, they wanted to win, and made it happen.”

Stredicke was the first off the court Thursday, beating BC High’s Chris Curran 6-0, 6-3. Normally a power hitter, Stredicke credited his win to a change in strategy.

“Usually I try to out-hit them, but this time I was more trying to place the ball and out-rally,” Stredicke said.

Adhvay Karthikeyan and Kadhir Kumaran brought Winchester within a point of the upset, taking No. 2 doubles 6-2, 6-4 over BC High senior twins Ollie and Danny Fearing. With Eagles (13-5) No. 1 doubles team Alexander Fine and Ryan Berns having already won 6-3, 6-3 over senior captains Thomas Andrews and Jamie Binda-Dunn, Winchester would need one more point from either freshman Henry May at No. 1 singles or senior captain Sam Song at No. 3 singles.

After gutting out a close win in the first set, Song took control in the second to clinch the match. Darien Nasseh tried to drill a forehand deep into Song’s side of the court, but the ball went too far, wrapping up Song’s 6-4, 6-1 victory.

“We got off to a really quick start, and you could hear it,” Song said. “Everyone was going for every ball. I could see all the hype, and I think that’s what pushed us beyond our expectations.”

Andrew Garofoli beat May at No. 1 singles for BC High, 6-2, 6-3. Curran, Berns and the Fearings played their final match for the Eagles.

“They were a great group of kids,” said Eagles coach Lance Hutchinson. “They made the state tournament every year. They won a bunch of tough matches. There was great leadership also, a lot of camaraderie, but today, unfortunately, one team has to win, and one team has to lose.”