The season began with Gary McAllister still managing Leeds, and they appeared to be in automatic promotion contention after a promising start.

However, a humiliating FA Cup exit to Football Conference side Histon saw the team's form completely collapse, and with any hope of automatic promotion having all but ended even before Christmas Day, McAllister was sacked.

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.

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).

3Although intended to be undisclosed, chairman Ken Bates revealed on Yorkshire Radio on 19 May 2009 that the compensation paid to the player's former club was £300,000.

1Player was at the club on a non-contract, pay-as-you-play deal which include a clause in which either party could cancel the agreement with 7 days notice.