On 25 May 2006, Picken later joined the club on a permanent basis, signing a two–year contract. His first game after signing for the club on a permanent basis came in the opening game of the season, where he made his first start, in a 3–0 win over Bournemouth. He began playing from a left–back position to right–back position, as the season progressed, and then scored his first Chesterfield goal on 17 February 2007, in a 3–0 win over Port Vale. Despite suspension and injury, Picken made 39 appearances and scored once in his first full season at Chesterfield.