The Ottawa Senators signed McCleary as an undrafted free agent upon his graduation, and he spent the majority of the 1993–94 season with the Thunder Bay Senators of the Colonial Hockey League (CoHL). He moved up to the Prince Edward Island Senators of the American Hockey League (AHL) in 1994–95 but missed three months of the season after suffering retinal damage to his right eye when he was hit in the face by a stick. Upon his recovery, McCleary returned wearing a visor that he would retain throughout his career.