Bolton confirmed that they would not be taking up the option of signing Ebi Smolarek, Sébastien Puygrenier or Ariza Makukula after the end of the previous season, and all returned to their parent clubs.

[1] Bolton announced on 6 May 2009 that long serving goalkeeper Jussi Jääskeläinen had been granted a testimonial against Hibernian at the Reebok Stadium on 8 August.

[3] On 12 June, the club published its full set of pre-season fixtures which included a three-game tour of Germany and the Netherlands, where the team met Borussia Mönchengladbach, Den Bosch and FC Eindhoven.

[4] The first team finished its pre-season unbeaten, drawing all their games with the exception of Den Bosch, which they won 2–1, with Sam Ricketts and Kevin Davies scoring.

[6] This immediately put pressure on manager Gary Megson, with some fans chanting for his resignation during Bolton's 1–0 League Cup victory at Tranmere Rovers three days later.

[15] This, however, was Bolton's last win for seven games as they went on a run that included two successive 4–0 defeats to Chelsea, the first away in the League Cup,[16] the second at home three days later with Zat Knight scoring another own goal.

[19] This run off defeats was halted after a 1–1 draw at Fulham[20] but a 2–1 loss to fellow strugglers Wolverhampton Wanderers[21] led to renewed pressure on the manager and calls for him to be replaced.

The game ended in a 2–2 draw after Bolton had led 2–0, the home fans loudly booing the decision to replace goalscorer Ivan Klasnić with Gavin McCann while leading 2–1.

[42] The January transfer window saw Bolton loan Vladimír Weiss from Manchester City[43] and Jack Wilshere from Arsenal,[44] as well as bringing in American international Stuart Holden[43] on a free transfer, all until the end of the season, while the club loaned out Nicky Hunt to Derby County,[45] Tope Obadeyi to Rochdale[46] and Mark Connolly to St Johnstone,[47] all again until the end of the season.

[48] February started with a 0–0 draw at home to Fulham[49] after which it was confirmed that Gary Cahill had suffered a blood clot in his arm and could be out for the rest of the season.

Bolton then went on another poor run with four successive defeats to Everton,[61] Manchester United,[62] Aston Villa[63] and Chelsea,[64] failing to score in the process.