 In his first season in charge, he successfully consolidated the club's position in the division, and the following year they were promoted as champions, while also reaching the 2003 Scottish Challenge Cup Final - Stewart played the entire match.He also brought in another old playing colleague, veteran striker Owen Coyle, as a player-coach, and when Black moved on Leicester City, Stewart appointed Coyle as his assistant.In 2004–05 Airdrie United finished 5th, and at the end of that campaign Stewart retired from playing, while Coyle left to manage St. Johnstone.