The Des Moines Oak Leafs began play in 1961 in the USHL playing out of the Des Moines Ice Arena, which still exists today. The Oak Leafs spent two years in the U before moving up to play professionally in the IHL, which battled against other midwestern teams. However, Iowa was a new state for the league which in 1963 consisted of teams from Ontario, Michigan, and Indiana.
The Oak Leafs got off to a good start in the IHL, making the league finals 1965 after posting 39 wins in 70 games. They would be led by John Annable during this time, who would go on to be the club's all-time leading scorer with 403 points in 338 games. The Oak Leafs would lose the 1965 finals to Fort Wayne.
The team would continue play in the IHL through 1971-72, with another finals appearance in 1971 where they would lose to Port Huron. In all, the team had a good run, making the playoffs in six of 10 seasons. After 1971-72, the team would rebrand and become the Des Moines Capitols, leaving behind the logo of the funny little hockey player that donned the front of their jerseys.