Skipworth was drafted 53rd overall by Adelaide in the 2000 AFL Draft and made his AFL debut in round 1 of the 2001 season against the Sydney Swans at the Sydney Cricket Ground, before playing another four matches that year and kicking one goal. Skipworth was de-listed at the end of the 2002 AFL season after failing to add to his overall matches tally, before being picked up by the Crows again for the 2003 season via the rookie draft (pick number 13 overall). Skipworth was elevated to the senior list again midway through that season after teammate Andrew Crowell sustained a serious knee injury and was placed on the club's long-term injury list.