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 with the Ulster Cup and Coleraine underlined their credentials by winning this competition. They carried their form into the league, with Shiels' men sitting top of the league after eight matches. The club remained in the hunt for the league title until the end of the season when they were pipped for the honours by Crusaders. This was to be the high-water mark of Shiels' time at Coleraine as the club began to slip back into a more mid-table position, despite some comparatively heavy investment in playing staff. During the 1999–2000 season, things came to a head when the club