The 2021 Pinstripe Bowl was a college football bowl game played on December 29, 2021, with kickoff at 2:15 p.m. EST and televised on ESPN. It was the 11th edition of the Pinstripe Bowl, and was one of the 2021–22 bowl games concluding the 2021 FBS football season. Sponsored by the New Era Cap Company, the game was officially known as the New Era Pinstripe Bowl. The Terrapins would score 54 points while only allowing 10 en route to their first win in a bowl game since the 2010 Military Bowl.

The Pinstripe Bowl is a National Collegiate Athletic Association (NCAA) Division I Football Bowl Subdivision (FBS) college football bowl game that is held at Yankee Stadium in The Bronx, New York City. First played in 2010, the game is organized by the New York Yankees, primary tenants of the venue, and is currently affiliated with the Atlantic Coast Conference and Big Ten Conference through 2025. The game previously had ties with the Big 12 Conference and the Big East Conference.