2008–09 Dundee United F.C. season

Last season's top scorer Noel Hunt left in July to join his brother Stephen at English side Reading.

The club began pre-season by winning the Keyline Cup in Oban on 12 July[17] before embarking on a short trip to Dublin where they played two friendlies against local sides.

[18] Upon returning to Scotland, United beat Raith Rovers 4-0 and fellow Fife side Dunfermline Athletic 3-2[19] before a match against Barcelona for the second year running.

[21] United also sent sides to play in victories against Cowdenbeath,[22] Arbroath,[23] Forres Mechanics,[24] Dundee North End[25] and Blairgowrie.

In April, the club racked up an 8–0 win at Brora Rangers to mark the opening of the ground's new floodlights, with Andis Shala scoring a hat-trick.

The run of victories saw first league goals for summer signings Scott Robertson and Roy O'Donovan, with three clean sheets for goalkeeper Lukasz Zaluska.

United's final trip to Glasgow resulted in a narrow 2–1 loss against Celtic, with defeats against Heart of Midlothian and Rangers to close the season.

United beat East Stirlingshire 4–0 at Ochilview Park in the Scottish Cup fourth round, with goals from Prince Buaben, Darren Dods, Jon Daly and Johnny Russell.

Last season's runners-up United began their League Cup campaign away to Cowdenbeath, where a hat-trick from Jon Daly helped them to a 5–1 win.

[35] In August, Craig Levein's pursuit of Roy O'Donovan ended with a season-long deal for the Sunderland striker,[36] although he was recalled in January, as was Willo Flood, ahead of his transfer to Celtic.

On transfer deadline day, Paul Caddis moved from Celtic Park until the end of the season, with Australian midfielder James Wesolowski joining on a similar deal from Leicester City although his spell was cut short by injury.

The club sold only one player during the season, with Noel Hunt joining his brother Stephen at English side Reading for around £600,000.

Towards the end of February, midfielder Greg Cameron moved on loan to Irish outfit Shamrock Rovers, managed by former United player Michael O'Neill and Fraser Milligan departed to Montrose on a similar deal shortly afterwards.

Action during the 2–0 SPL home win against St Mirren
League positions
United players warming up before the cup match against East Stirlingshire