The 2008–09 season was Leeds United F.C.'s second consecutive season in the third tier of English football and for the second year running saw them finish in the play-offs in League One. Gary McAllister started the season as manager, but after a poor run of games in late 2008, his contact was terminated and he was replaced by Simon Grayson. After a nervy first few games, Grayson lifted the side from 8th to 4th, resulting in a place in the play-offs. During this time, the club recorded an incredible 11 consecutive home wins. Although to the heartbreak of Leeds fans, the club failed in the play-offs again, being defeated by Millwall in the semi-finals. During the season, Jermaine Beckford scored 34 goals in all competitions - the highest in the country. Once again, the club received the highest attendance outside the Premier League on three occasions; the largest in the play-off semi final, recording a crowd of over 37,000. Off the pitch, the club made a profit for the first time in years.

This is a list of the significant events to occur at the club during the 2008–09 season, presented in chronological order (starting from 26 May 2008 and ending on 14 May 2009). This list does not include transfers or new contracts, which are listed in the transfers section below, or match results, which are in the matches section.

Appearances (starts and substitute appearances) and goals include those in The Premiership, The Championship (and playoffs), League One (and playoffs), FA Cup, League Cup, Football League Trophy, and UEFA Cup.
¹Player first came to the club on loan and was transferred the following year.
²Player is at the club on loan
Squad includes players registered with the club on the last day of the season (14 May 2009) only.

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