Winckowski primarily pitched out of the bullpen in 2024 but made six spot starts for the Red Sox. The team hopes to utilize him solely as a reliever in 2025, although he remains a viable option for rotation depth if needed.

Josh Winckowski pitched in relief during the game, allowing a two-run homer to Jonatan Clase in the seventh inning. His appearance came after the Red Sox had been unable to contain the Blue Jays' offense, contributing to the team's overall struggle as they sought to secure a series sweep.

Josh Winckowski allowed a two-run homer to Jonatan Clase in the seventh inning, contributing to the Red Sox's defeat. He was on the mound in relief as Boston's bullpen faced challenges against a robust Toronto offense.

Josh Winckowski was replaced by Zach Penrod in the eighth inning after Aaron Judge's leadoff double. Winckowski's outing concluded with the team needing a fresh arm, and Penrod made his MLB debut, showcasing the team's depth in the bullpen.

Josh Winckowski faced Soto in the 10th inning, throwing a 2-2 sinker that allowed Soto to deliver the game-winning hit. His performance was a critical moment in a tightly contested game, which saw the Yankees capitalize on the bullpen's ability to keep the Red Sox scoreless for five innings.