He made his NHL debut in Ottawa in 1995–96, scoring 14 points in 75 games. The Senators traded McCleary, along with a draft pick to the Boston Bruins for Shawn McEachern following the season. He appeared in 59 games with the Bruins but was unable to come to an agreement on a new contract for the 1997–98 season. As a result, he signed to play in the International Hockey League (IHL), splitting the season between the Las Vegas Thunder and Detroit Vipers.