Pearson moved to Sheffield Wednesday in 1987. He won the League Cup as Sheffield Wednesday captain, during the 1990–91 season, being selected as "Man of the Match" in the final at Wembley. In the same season, he also helped Sheffield Wednesday win promotion to Division One. During the 1992–93 season, he helped Sheffield Wednesday reach both domestic cup finals, but broke his leg in the League Cup semi-final, and therefore could not play in either final. In all, Pearson made more than 200 appearances for the Owls, scoring 14 league goals – including the club's first in the Premier League in a 1–1 draw with Everton at Goodison Park on the opening day of the 1992–93 season.