Pre-season was completed by a mini-tour of Greece, drawing 1–1 against previous UEFA Cup opponents Aris Thessaloniki before losing to AEK Athens 1–0.

This was followed four days later by a home 2–1 Carling Cup defeat to League One side Northampton Town, a result not helped by the sending off of Gary Cahill.

After an international break, Bolton returned to action by facing Fulham at Craven Cottage but performed poorly in another 2–1 defeat, Kevin Davies scoring late on.

The first reported murmurings of discontent amongst the fans against the manager followed a 2–0 defeat at Tottenham Hotspur in Harry Redknapp's first game in charge of the home team on 26 October.

[5] The pressure was eased somewhat with a 2–0 derby victory over Manchester City on 2 November, a Richard Dunne own-goal adding to Ricardo Gardner's first league goal in six years.

[6] Winning the award seemed to have a detrimental effect on the team as two successive defeats followed to high flying Chelsea and Aston Villa.

A similar fate almost befell the team in the next home game against Tottenham Hotspur, Darren Bent scoring twice in two minutes to cancel out early goals from Sébastien Puygrenier and Kevin Davies.

Due to international fixtures and the club's early departure from the FA Cup, only two games were played in February, a 3–0 away defeat to Everton and a 2–1 victory over West Ham, Bolton completing a double over the London side.

A 1–0 result at Portsmouth was then followed by four successive draws stretching into May, Aston Villa, Sunderland and Hull City taking points at the Reebok whilst a local derby at Wigan Athletic.

The season finished with a 1–0 derby defeat at Manchester City Statistics accurate as of match played 24 May 2009 Supplier: ReebokSponsor(s): Reebok