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
Kenny Shiels lost consecutive matches to Limavady United in the Gold Cup and Linfield in the league, causing Shiels to tender his resignation. According to the official club website Shiels was manager of Moyola Park from January 1999 to December 2000, although these dates overlap in part with his time at Coleraine. Nonetheless Shiels was in charge of the club and even signed a youthful Ivan Sproule for them. Shiels next appointment was at Ballymena United, where he was confirmed in the managerial chair on 2 January 2001. The club were battling relegation and ultimately Shiels was unable to prevent the club