In 1985–86 the club were relegated to Division Two after finishing second-from-bottom of Division One. However, they made an immediate return to Division One by winning Division Two at the first attempt. The 1987–88 season saw a second League Cup win with a 2–1 defeat of Shildon in the final, as well as another FA Cup first round appearance – a 4–2 loss to Halifax Town in a home match played at Hartlepool United's Victoria Park. They went on to win back-to-back Division One titles in 1988–89 and 1989–90; The 1989–90 season also saw a third League Cup win, beating Whitby Town 5–2 in the final, as well as a seventh appearance in the FA Cup first round, this time losing 1–0 at Lincoln City.