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
Kenny Shiels several signings, the club, remained bottom of the league and a 2-0 loss against Alloa Athletic on 12 April 2014 confirmed relegation for Morton. Despite being relegated, it was initially believed that Shiels would stay on as the Greenock Morton boss for the next season, and attempt to return Morton to the Championship, similar to his experience during his time at Coleraine. However, Shiels resigned on May 2014 following a 10-2 defeat by Hamilton Academical which ended a poor season and relegation from the Scottish Championship. Immediately after the match, Shiels said in the post-match press conference, that he was