Kenny Shiels the League Cup Final, where they upset the odds by beating Celtic 1–0, with Dieter van Tornhout scoring the crucial goal in the 83rd minute. Killie's joy was tempered by the death of Liam Kelly's father, Jack, who suffered a fatal heart attack at the final whistle of the game. On the win, Shiels stated the team "are thinking more about Liam (Kelly) than our triumphalism". He then told BBC Scotland's Jonathan Sutherland, winning the cup is "unbelievable", in addition "a great emotion" for the Kilmarnock's supporters. Following his side's historic cup win, Shiels announced his intention to stay at
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