 The same season, Baldwin aided the U's to second position in League One and promotion to the second tier for the first time in the club's history during the 2005–06 season.On 25 November 2006, Baldwin scored his first and only league goal for Colchester in a 3–0 victory in the Essex derby over rivals Southend United.Baldwin agreed to another two-year contract extension in February 2007 on the back of Colchester's success in their debut season in the Championship, with Baldwin a regular starter.