The 2005–06 season was the 97th year of football played by Dundee United, and covers the period from 1 July 2005 to 30 June 2006. United finished in ninth place for the second consecutive season and meant they had only finished in the top six once in the six seasons since the split was introduced.

United finished the 2005/06 SPL season in 9th place with 33 points, narrowly beating Falkirk (10th) and Dunfermline Athletic (11th) on goal difference. United exited all three cup competitions at the first stage. Between April and early-May, United lost six consecutive games, including losses to the three clubs which finished below them in the league.

The much-anticipated UEFA Cup campaign ended in disappointment with an away-goals defeat to Finnish side MyPa (after United surrendered a two-goal lead), and a CIS Insurance Cup defeat to Inverness CT followed, although an incredible 5–4 away win over Motherwell brought some early-season cheer. United also exited the Scottish Cup at the first hurdle, bowing out 3–2 to Aberdeen after again throwing away a two-goal lead.

Little league success followed, and the Terrors finished ninth on goal difference, thanks to a late Collin Samuel equaliser against Motherwell on the season's final day. In mid-January, Gordon Chisholm was sacked, with United favourite Craig Brewster leaving Inverness CT to take over. Brewster would go on to win just one league game all season and leave United before 2006 was out.

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