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 to join Rangers. He scored a goal, as well as, setting up two goals in his first appearance, in a Scottish League Cup tie against East Fife on 7 August. A week after he sustained an injury during a match which ruled him out for weeks, On 2 September 2012, Shiels scored his first league goal, as well as setting up a goal, in a 5–1 win over Elgin City. After scoring two goals in three games, Shiels scored against the Scottish Premier League side Motherwell, in a Scottish League Cup tie. Then, in the Scottish Cup, Shiels scored twice