After attending the Maple Leafs' training camp in September 2008, Reimer was assigned to the Toronto Marlies of the American Hockey League (AHL). After starting the season with the Marlies, he was assigned to the Reading Royals of the ECHL. He was recalled by the Marlies and recorded his first AHL win by a score of 3–2 in a shootout on December 27, 2008, against the Manitoba Moose. In two stints with the Marlies, Reimer had a record of one win and two losses, with a goals against average (GAA) of 3.28 and a .882 save percentage. With the Royals, Reimer had a record of ten wins, seven losses and three ties. At the ECHL trade deadline, Reimer was moved to the South Carolina Stingrays, a team that had gone through eight goaltenders during the season. The deal was facilitated to expose Reimer to post-season experience, as the Royals were out of playoff contention. While with the Stingrays, Reimer helped them win the 2009 Kelly Cup championship. Recording four wins and one shutout over eight games in the post-season, he was named the ECHL Playoffs Most Valuable Player.