Scottish League Cup
Ayr United reached their first Scottish League Cuop semi-final in October 1950 and were in sight of their firt ever cup final with 7 minutes to go. Motherwell had other ideas and slotted in two late goals to win 3-2.
In October 1969 Celtic stood in the way of Ayr and that Cup Final place and a 3-3 draw gave hope for the replay. The Somrset Park faithful were treated to another glorious defeat by 2-1 against the former Furopean Champions.
United thought their best chance had come in November 1980 when they were drawn in a two leg semi-final to play Dundee. The home match ended 1-1 but in the second match at Dundee's Dens Park United were 2-1 ahead late on. History repeated itself and United lost two late goals to go out by 3-2.
That ellusive Cup Final would just not materialise. But for Ayr United the world turned in February 2002 when, as a 1st division team, they beat Premier league side Hibernian 1-0 at Hampden Park in the semi-final of the CIS to earn themselves the right to play Rangers in the Scottish League Cup Final on 17th March 2002 - their first ever senior Cup final (their were lower divisions Cup Finals earleir).
Cup Final day ended in a 4-0 win for the Glasgow team, a score that was always the likely outcome, but the day belonged to United and the 12,000 supporters who followed them to the match. 
Cup Semi-Finalists
1950/51, 1969/70, 1980/81
Cup Finalists
2001/02