 Injury ruled him out of the 2005–06 season completely and he signed a one-year deal with Leyton Orient at the beginning of 2006–07.On 5 February 2007, Chambers signed a two and a half-year contract which keeps him at the club until the end of the 2008–09 season.His performance in Orient's 3–1 home win over Port Vale on 20 October 2007 earned him a place in the League One Team of the Week.