The 2008–09 season was Middlesbrough's eleventh consecutive season in the Premier League. They were relegated at the end of the season. They were knocked out of the League Cup in the third round and knocked out of the FA Cup in the quarter-finals (sixth round).

Gareth Southgate continued as manager under chairman Steve Gibson. Before the season, Southgate was considering whether to continue with the traditional role of a club captain, but later decided that Emanuel Pogatetz would continue being captain following his performances in the final ten games of the previous season.

Middlesbrough's kits were produced by Erreà for the fifteenth and final season, and sponsored by GPS manufacturer Garmin. Back at the start of 2008, the club ran a poll to decide whether the club should return to the white band of prior seasons. The votes came out in favour of the band, and it was then up to the fans to decide between three different designs. The winning shirt was announced on 7 May 2008 to be choice A – the white band with a curl. The away kit, announced on 17 July 2008, would see a return to the popular black and blue striped kit worn by Jack Charlton's side of the mid-1970s.

Middlesbrough net spending over the 2008 summer transfer window was almost nil, as money spent bringing in new faces was matched by money brought in through player sales, though it had only been half a year since Afonso Alves' club-record signing during the previous season.

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