Red & Black Advance to Final Four With 38–21 Quarterfinal Win Over Lincoln-Sudbury

Author: Tommy Kowalczuk, WHS Class of '26

The Winchester Red & Black football team continues its postseason surge, earning a hard-fought 38–21 victory over Lincoln-Sudbury in the MIAA Division 2 quarterfinals and punching its ticket to the Final Four. The win showcased a balanced attack, dominant defense, and standout special teams play, proving the Red & Black are a force to be reckoned with as the playoffs continue.

Winchester High School advances to the Final Four.

Offensively, Gianni Depremio was unstoppable, scoring three touchdowns and consistently moving the chains, while Ronan O’Connell added two more scores to keep Winchester in control. Ryan Martin contributed a receiving touchdown, and key punt returns helped swing momentum and set up scoring opportunities. The team’s efficiency and versatility on offense allowed them to capitalize on opportunities while keeping Lincoln-Sudbury on their heels.

The defense was equally impressive. Senior Quinn Pimentel, when asked about the unit’s performance, praised his teammates and coaches: “Lincoln-Sudbury is a fantastic football team. I couldn’t have done it without Coach Dembowski, Bryan Harrison, Andrew Haigis, and Will Bologenese — they all played amazing. It’s a really good feeling to get this far. I think we worked pretty hard, and playing the best team in the state next week will definitely be a big challenge that we’re excited for.”

On how the defense maintains its edge, Pimentel added: “The practice helps a lot, the coach’s play calling is incredible, and I feel like we’ve been dominant working and playing together.” Indeed, the Red & Black suffocated Lincoln-Sudbury’s offensive opportunities, making crucial stops and maintaining pressure throughout the game. The team’s preparation, communication, and cohesion were evident on every snap.

With the final score at 38–21, Winchester moves on to the Final Four, where they’ll face the top competition in the state - Catholic Memorial. With contributions from multiple offensive weapons, a dominant defense, and a strong team mentality, the Red & Black enter the next round with momentum, confidence, and the experience of overcoming tough playoff competition.