His rights ultimately released by the Bruins, McCleary signed with the Montreal Canadiens as a free agent in 1998, appearing in 46 NHL games in 1998–99. Early the following season, he again suffered a severe injury to his right eye, suffering a severed tear duct when he was hit in the face by an errant skate. He recovered, splitting the early part of the season between the Canadiens and the Quebec Citadelles in the AHL.