Dawson made his Bury debut on 9 August 2008 on the opening day of the season with a 1–0 win over Brentford at Gigg Lane. Since making his debut for the side, Dawson quickly established himself in the first team, partnering with Brian Barry-Murphy in central midfield. He then scored his first goal for Bury on 18 October 2008 in a 3–1 win at Dagenham & Redbridge. After being suspended against Darlington in the Football League Trophy campaign for picking up his fifth yellow card this season, Dawson returned to the first team and it wasn't until on 6 December 2008 when he scored again, in a 1–1 draw against Macclesfield Town. However, in a 1–0 defeat against Brentford on 28 February 2009, Dawson was sent–off for a second bookable offence. Up until his sending off, Dawson started every matches for the side since the start of the season. Despite being suspended for the second time this season, the club was unsuccessful to reach promotion to League One. Nevertheless, Dawson was awarded 4 awards: Bury Times Player of the Year, Disabled Supporters Player of the Season, Billy Ayre Memorial Official Website Player of the Season, and Forever Bury Player of the Season. Manager Knill praised Dawson's role this season at Bury. In his first season at Bury, Dawson made the total of 47 appearances and scoring 2 times in all competitions.