Skipworth returned to the Essendon Football Club, where he served as the midfield coach until the conclusion of the 2019 Season.
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.
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.