Orr played as regular early in the 2005–06 season with the Bruins, but was shortly waived, where on November 29, 2005, the New York Rangers claimed him off waivers.

Ovechkin was uninjured, but NHL Senior Vice President and Director of Hockey Operations Colin Campbell termed Orr's infraction "reckless.

[3] His next year with the Maple Leafs was cut short after suffering a concussion in a fight with Anaheim Ducks' enforcer George Parros.

Orr played in 44 of 48 games in the lockout-shortened 2012–13 season with Toronto, scoring one goal and adding three assists while leading the NHL in penalty minutes, with 155.

On October 1, 2013, while playing for Toronto in their home opener against the Montreal Canadiens, Orr engaged once again with George Parros, now of the Habs, in the third period.

[5] Orr failed to make the Maple Leafs' roster out of training camp for the 2014–15 season and was assigned to the Toronto Marlies after clearing waivers.

[6] On October 3, 2015, Orr signed a contract to play in the American Hockey League for the Stockton Heat, the farm team for the Calgary Flames.

[7] On May 14, 2019, the Danbury Colonials of the Tier III junior level North American 3 Hockey League announced that Orr had joined the ownership group and would serve as the organization's managing partner.