1991 Scottish Challenge Cup Final

Hamilton Academical entered the first round with 20 other clubs from the First and Second Divisions; six clubs received random byes into the second round. The club was drawn against Alloa Athletic in the first round at home and won 5–1 at Douglas Park.[3] In the next round Hamilton Academical travelled to Partick Thistle where they won 2–1[3] to progress to the quarter-finals. With eight clubs left in the competition, Hamilton faced East Fife away from home and won 3–2 to qualify for the semi-finals where they played Raith Rovers at Douglas Park to win 2–1 and progress to the final;[3] their first national final since 1935.

In the first round Ayr United played Dundee in a repeat of the previous season's final, which the club lost 3–2 after extra time. This time Ayr United won the match 2–0 at Dens Park to progress to the second round.[3] The next round was a match at Ochilview Park to face Stenhousemuir where it ended 2–0 to Ayr United.[3] With eight clubs left in the competition, the club played Stranraer at Somerset Park and won 2–0 for the third consecutive round and progress to the semi-final. The draw for the semi-final paired the club with Queen of the South which Ayr United won 3–2 to reach the final of the tournament for the second year in a row.[3]

Both Ayr United and Hamilton Academical played two games each at their respective homes of Somerset Park and Douglas Park, and two away games in the rounds preceding the final. Ayr United scored a total of nine goals and conceded only two before the final, compared with Hamilton Academical's twelve goals scored and five conceded. Ayr United kept a total of three clean sheets whilst Hamilton Academical kept none. This was the first appearance for Hamilton in the Scottish Challenge Cup Final, whereas Ayr United had been defeated in final of the previous season in the competition's inaugural year.[3]