Jimmy Nicholl followed Calderwood when he took over as manager at Aberdeen, again serving as his assistant until the two parted company with the club in May 2009. He resumed his partnership with Calderwood at Kilmarnock in 2010. Nicholl was appointed manager of Cowdenbeath in June 2010, but he left Cowdenbeath at the end of the 2010–11 season after they were relegated from the First Division. Nicholl was then appointed assistant manager of Kilmarnock for a second time, by Kenny Shiels on 15 June 2011. Kilmarnock won the 2011–12 Scottish League Cup under Shiels and Nicholl, but Shiels was sacked by Kilmarnock
Greenock Morton F.C. the relegation playoff by a single goal. Irons was sacked in September 2009 and replaced October by James Grady until the end of the season. Grady was removed from the club in May 2010, and replaced by Allan Moore. Allan Moore was sacked after a 5–1 defeat at home to Livingston on 23 November 2013. His replacement Kenny Shiels was given a contract until the end of season 2014–2015, but failed to reverse the slide towards relegation from the Scottish Championship, which became a reality on 12 April 2014 after a 2–0 away defeat by Alloa Athletic. Shiels resigned after