Dean Shiels last home match of the 2008–09 season, when he scored the first goal in a 2–0 victory over Crystal Palace. Shiels scored six goals in 42 games during the 2009–10 season. However, during the 2010–11 season Shiels lost his place in the Doncaster starting line-up. He was loaned to Kilmarnock in July 2011 and his contract was mutually terminated in January 2012. Shiels signed a six-month loan deal with Kilmarnock, managed by his father Kenny Shiels, in July 2011. Shiels made his first appearance for Kilmarnock on 30 July 2011, in a goalless draw against Motherwell at Rugby Park, coming
Dean Shiels cost-cutting that is due to take place at the club; manager Ally McCoist refuted this. On 8 February 2014, Shiels scored a hat-trick in the Scottish Cup, as Rangers won 4–0 against Dunfermline Athletic. On 10 June 2016, Shiels left Rangers after his contract came to an end. He had made 43 appearances for Rangers in his final season with the club, as they won promotion to the Scottish Premiership. On 25 August 2016, Shiels signed for Dundalk in the League of Ireland Premier Division citing the "lure of European football" as one of the things that attracted him to