The 1995–96 season was the 94th season in which Dundee competed at a Scottish national level, playing in the Scottish First Division. Dundee would finish in 5th place, their lowest league position since the 1938–39 season. Dundee would also compete in the Scottish League Cup, the Scottish Cup and the Scottish Challenge Cup, where they were knocked out by Clyde in the 3rd round of the Scottish Cup, and by Stenhousemuir in the quarter-finals of the Challenge Cup. They would make it to the final of the League Cup, before being defeated by Aberdeen at Hampden Park.