Skipworth had his best AFL season in 2005, in which he played 21 matches, including three finals matches (against St Kilda, Port 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).