Shamrock Rovers had won the League Cup once previously, in 1976–77, and had lost on their two previous appearances in the final. In the 1986–87 season they would go on to win a League and FAI CupDouble, with Dundalk finishing as runners-up in both competitions.
Both sides went into the match with much-changed sides due to a number of injury problems. Dundalk had three players making debuts, including local-league player Paul Matthews who was signed as cover on New Year's Eve; while manager Turlough O'Connor, was obliged to be listed as '13th player' on the team-sheets. Dundalk's Dessie Gorman missed two early chances before they were awarded a controversial penalty in the 39th minute, when Noel Larkin was adjudged to have fouled Tom McNulty near the goal-line in a tussle for possession. Martin Murray scored the resultant spot-kick, despite it being weakly struck. In a match described as "disappointing" in press reports, both sides failed subsequently to create any real chances, with Martin Lawlor and Harry McCue performing well at the centre of a makeshift Dundalk defence, and new Rovers player-manager, Dermot Keely (a former Dundalk stalwart) dominating at the back for his side. Dundalk goalkeeper, Alan O'Neill, was forced into making two late saves as they held out. The win was Turlough O'Connor's first trophy as Dundalk manager, and the club's first since 1981–82.