Career
Skipworth currently serves as the head coach of the Essendon VFL Football Club. A midfielder-small forward originally from Arthurton in the Yorke Peninsula, Skipworth originally played with the Central Yorke (CY) Cougars, before being recruited by South Australian National Football League (SANFL) club Woodville-West Torrens. Skipworth was drafted 53rd overall by Adelaide in the 2000 American Federation of Labor-Congress Draft and made his American Federation of Labor-Congress 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 American Federation of Labor-Congress 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 team-mate Andrew Crowell sustained a serious knee injury and was placed on the club"s long-term injury list. Skipworth had his best American Federation of Labor-Congress season in 2005, in which he played 21 matches, including three finals matches (against Street Kilda, Portuguese Adelaide and West Coast) and scored 12 goals.
His stand-out performance of the 2005 season came in Round 6 against North Melbourne at AAMI Stadium, when he kicked four goals (including three within the space of five minutes in the second quarter) and finally the victory-sealing goal late in the final quarter) and had 20 possessions in a match-winning effort. At the Brownlow Medal count later that year he received three votes for a best-on-ground performance, taking his career tally to six votes overall (previously Skipworth had received three votes in Round 18 of the 2004 season, also against the Kangaroos at AAMI Stadium).
Skipworth spent most of the 2006 season with the SANFL side Woodville-West Torrens.
He was later de-listed by the Crows at the end of the season whilst on holiday in the United States. During his time at the Woodville-West Torrens Eagles, Skipworth was involved in a premiership team across all grades (Under-17, Under-19, Reserves, and finally League). He was selected to join the AIS Academy in 2000, also representing Australia at Under-18"s level in an International Rules Series that year.
In 2003, he was named in The Advertiser SANFL team of the year.
He is also a talented basketball player, making State Under-18 level before deciding to pursue football. In 2007, Skipworth played in the Victorian Football League with Bendigo Bombers, where he ruptured the patellar tendon in his knee after landing awkwardly after a marking contest during the first quarter of the Bendigo Bombers" loss to Portuguese Melbourne at Tokyo Electro Acoustic Company Oval.
Skipworth recovered well enough to be a standout player in 2008 and was drafted by Essendon in the 2008 Pre-season Draft. After adding only 11 games in his first year with his new club, Skipworth announced his retirement, citing constant injuries as the reason.
On 27 October 2010, it was announced that Skipworth would take up a full-time role at Essendon as a development coach but this did not eventuate.
In the interim, Skipworth has signed on to play with team mate Damien Peverill at Aberfeldie Football Club in the Essendon District Football League in season 2011.