Stewart was in charge of the side during the 1920s when the club enjoyed success by reaching two FA Cup finals, losing in 1925 before becoming the only team from outside England to win the competition in 1927. They also finished as runners-up to Huddersfield Town in the 1923–24 First Division season, missing out on the title after failing to win their final game of the season. The later years of the decade saw a steady decline as the club's finances dropped and by 1931 the club had been relegated to the Third Division South. Following a 19th place finish in 1933, Stewart resigned from the role after 22 years.