The 1958–59 season was the 67th season in Liverpool F.C.

's existence, and was their fifth consecutive year in the Second Division.

The club finished fourth for the second consecutive season, seven points outside the automatic promotion places.

Liverpool lost their first match in the FA Cup to Worcester City, then in the Southern League, and one league below the Football League at that time.

The Third Round match finished 2-1 to Worcester City.