2001 Scottish Challenge Cup final

The first round draw brought Queen of the South to face Airdrieonians at the Excelsior Stadium for the second consecutive season[3][4] with the home team emerging 2–0 victors.[4] The second round was an away game at rivals Albion Rovers with Airdrie producing a 4–1 win[4] to progress to the quarter-finals. Just like the previous season Airdrie were drawn against Clydebank in the quarter-finals[3][4] and again emerged winners with a 2–1 victory.[4] The semi-final draw paired the club with Brechin City at home and it took penalties to separate the sides with The Diamonds winning 4–3 after a 1–1 draw after extra time to progress to the final.[4] Airdrieonians reached the Scottish Challenge Cup final for the third time, and second consecutive season since winning the 1994 final against Dundee and defeating Livingston the previous season to win the 2000 final.[3]

Alloa Athletic were drawn against East Stirlingshire away from home in the first round at Firs Park[5] and produced a 1–0 victory[4] over the club. The second round draw saw The Wasps drawn against Inverness Caledonian Thistle[4] whom they defeated on penalties in the 1999 final,[6] with the game being decided in extra time again with Alloa Athletic emerging 3–2 winners after a 1–1 draw after 90 minutes.[4] Another home game was drawn in the quarter-finals with Stranraer providing the opposition which saw Alloa Athletic win in extra time for a second consecutive game by winning 4–3[4] to progress to the semi-finals. The opposition provided was Clyde away from home with Alloa Athletic winning 1–0[4] to reach the Scottish Challenge Cup final for the second time after their 1999 triumph.

Airdrie and Alloa both played two games at home and two away each. In the process Airdrieonians scored nine goals and conceded three whilst Alloa Athletic also scored nine but conceded five. However, Alloa Athletic had kept a total of two clean sheets, both away from home, compared with Airdrie's one clean sheet. In Alloa's two games at Recreation Park it took extra time on both occasions before the club emerged winners. One of Airdrieonians' games had gone to extra time but then penalties before a winner was declared. This was Airdrieonians' third time competing in the Scottish Challenge Cup final,[1] whilst holding a 100% record after winning both the 1994 and 2000[3] finals. Alloa Athletic were appearing in the final for the second time in the club's history since defeating Inverness Caledonian Thistle on penalties after a 4–4 draw in the 1999 final.[6] On the road to that final Alloa Athletic had knocked out Airdrieonians in the second round at the Excelsior Stadium.[6]