Dundee United finished the Scottish First Division 1995–96 season in 2nd place, after being relegated from the Premier Division the previous season. Although missing out on the automatic promotion slot through winning the league, United won promotion through the play-off system, beating Partick Thistle 3–2 over two legs. United secured the play-off on the final day of the season, drawing with 3rd-placed Morton and finishing 2nd on goal difference.

United scored freely at home in the league, particularly in the second half of the season, including 8–0 and 6–1 wins over Dumbarton and a 6–0 triumph against Clydebank. This 19-goal swing was enough to provide the superior goal difference that secured 2nd place.

The cup campaigns brought little joy, with a 3rd round League Cup defeat to Motherwell and an agonising quarter-final Scottish Cup defeat to Celtic who scored twice in the last minute to win 2–1. Embarrassingly, the club lost on penalties to Stenhousemuir in the Scottish Challenge Cup final, although didn't concede during the entire tournament.

Off the pitch, United won the 'First Division Programme of the Year'.

Manager Billy Kirkwood continued to rebuild the team over the close season, bringing in Motherwell defender Rab Shannon, Rangers keeper Ally Maxwell and Neil Caldwell, also from Ibrox. Another two ex-Rangers players arrived before the start of the season, with Steven Pressley and Sandy Robertson both arriving from Coventry City. The Rangers connection continued when the Ibrox club made a bid of £1.5 million for Gordan Petric, which United accepted and this money helped to re-shape the team well into the new season. Also out the door went Juan Ferrari, walking out after not being promised a first team place, and the Brazilian Sergio left for Kuwait.

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