 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.