Osborne played in the National Hockey League (NHL) primarily as a checking winger between 1981 and 1995.
[1] Having walked onto the team, Osborne played his entire junior career for the Niagara Falls Flyers of the Ontario Hockey League (OHL) consisting of three seasons, between 1979 and 1981.
[3] He played a significant role on the Rangers, placed on a line with Anders Hedberg and Mark Pavelich.
[3][6] In his second stint with Toronto he was on an effective checking line with Bill Berg and Peter Zezel and helped the Leafs reach the conference finals in two consecutive playoff years (1993 and 1994), falling short each time of making it to the Stanley Cup Finals.
[8] He went on to play three more years with the Cleveland Lumberjacks of the International Hockey League (IHL) as a player-coach, retiring in 1997.