In other competitions, the club played a number of Premier League sides including a historic victory over rivals Manchester United in the FA Cup. The club's run in the FA Cup was the longest since 2003. Leeds also secured a place in the Football League Trophy area final, but lost to Carlisle United on penalties.

Simon Grayson became the first manager in five years to complete a full season as Leeds boss and celebrated it by winning the club's first promotion in twenty years. For the third season in a row, Jermaine Beckford was the club's top goalscorer with 31 goals in all competitions; Beckford was again named the League One Player of the Year, however lost out on the club's Player of the Year to Patrick Kisnorbo.

This is a list of the significant events to occur at the club during the 2008–09 season, presented in chronological order (starting from 15 May 2009 and ending on the final day of the club's final match in the 2009–10 season). 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 Championship (and playoffs), League One (and playoffs), FA Cup, League Cup and Football League Trophy.
¹Player first came to the club on loan and was transferred the following year.
²Player joined the club in 2008 as a scholar. He is presently a 2nd year scholar and is not currently signed to the club on professional terms.
Squad includes players registered with the club on the last day of the season (8 May 2010) only.

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