In the 2006 Scottish Cup Final versus Hearts, Skelton missed the crucial kick in the penalty shoot-out after a 1–1 draw.

[2] His miss denied Gretna their first major trophy, however they still qualified for the UEFA Cup as a result of their run to the final.

[4] Two days earlier, Skelton had scored the winning goal on his side's final SPL fixture against Hearts.

[8] On 22 December 2016, Skelton was tempted back to sign for Scottish League Two club Annan Athletic as a player, after he resigned as player-manager of Queen of the South on 7 November 2016 for personal reasons.

[12][13] Skelton was appointed caretaker manager of Queens on 18 April 2016 after James Fowler departed the club.

[17] On 31 December 2018, Skelton was reappointed manager of Workington, however he resigned in January 2019 after just six days and two games in charge of the club.