Winter was told that he would be leaving Aberdeen at the end of the 2006–07 season. He signed for Chesterfield on 20 July 2007, until the end of June 2009.
Winter was informed that he would be departing Aberdeen at the conclusion of the 2006–07 season. He signed a contract with Chesterfield for the remainder of the 2006-07 season and through June 30, 2009.