United suffered the agony of reaching three out of four Scottish Cup finals in the mid-1980s, only to lose them all by a single goal. First came a 2–1 defeat to Celtic in 1984–85, compounded by a 1–0 League Cup final loss to Rangers in the same season; then a 1–0 defeat in extra time to St Mirren in 1986–87; and finally, a last-minute 2–1 loss against Celtic the following year, despite being a goal ahead. A three-year gap ensued before the 1990–91 Scottish Cup final, which pitted Jim McLean against his brother Tommy, at Motherwell. The final was won 4–3 by 'Well, with United again losing in extra time. The sixth Cup Final loss was also the club's fifth final appearance in eleven years.