 After attracting interest from several clubs during the January transfer window, it was announced on 29 June 2007 that Bailey was discussing terms with Southend United of League One.He eventually signed with Southend on 3 July 2007 for a fee of £175,000.After winning the club's player of the year award for the 2007–08 season, Bailey was transfer listed on 5 June 2008 after failing to agree to terms over a contract extension.