Standing at 193 cm, Skipper won the 2003 best first year player for his original club the Western Bulldogs.
At the end of the 2009 season, Skipper was delisted from the Western Bulldogs, and picked up by Hawthorn with selection 13 in the Rookie Draft on 15 December 2009.
On the eve of the 2010 season, with the Hawks' ruck stocks thin, Skipper suffered another setback with a hamstring injury keeping him out of the team.
Hawthorn felt that new recruit David Hale and the raw talent of Brent Renouf, would make Skipper surplus to requirements for the 2011 season.
In the 2014 and 2015 seasons, Skipper played for Hoppers Crossing in the Western Region Football League.