Dempsey is a versatile right footed withdrawn forward, at times shooting from long distances and even scoring at club level from long range shots. However, he has also proven to be more of a threat the closer to goal he gets.
Known for his toughness and resilience, Dempsey played two games for New England Revolution with a broken jaw in 2004 before the team trainer diagnosed it, and upon his return, he played through the pain of a sprained ankle. Despite usually playing in wide positions, he frequently scores close-range goals and has scored repeatedly with diving headers in crowded situations.
His tenacity in midfield combined with his audacious close control dribbling skills frequently results in opponents fouling him, and Dempsey has gained a reputation for fierce play.