Kenny Shiels Rangers in 17 years on 27 November 2011, in a 1–0 victory at Rugby Park, with a Manuel Pascali goal in the 80th minute. After the match, Shiels said a win over Rangers was a "fantastic win" for the club, in addition, stated his opinion that people in Ayrshire, who are Old Firm supporters, are not real supporters for Kilmarnock. He wrote in his Daily Record columns that he was critical of fans would watch the Old Firm, rather than their local team. In the January transfer window, Shiels soon added his son, Dean, and Ben Gordon. He also helped
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