The 1958–59 season was the 21st season of competitive association football in the Football League played by Chester, an English club based in Chester, Cheshire.

Chester competed in the newly formed Fourth Division.

Alongside competing in the Football League the club also participated in the FA Cup and the Welsh Cup.

Source: rsssf.com Sumner, Chas (1 November 2011).

125 Years on the Borderline: The Complete History of Chester City F.C.