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 League Cup in his first season in charge, but he was sacked in June 2013 after he had been frequently punished by the Scottish Football Association for making controversial comments. Shiels was appointed manager of Scottish Championship club Greenock Morton in December 2013, and resigned in May 2014. He became Derry City manager in 2015. Shiels spent his entire playing career in Northern Irish football, both in the Irish Football League and at lower levels. Beginning at minor club Bridgend United, he subsequently appeared for Tobermore United, Coleraine, Distillery, Tobermore United again, Larne, Ballymena United, Tobermore United for a third