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.
[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 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.
In Alloa's two games at Recreation Park it took extra time on both occasions before the club emerged winners.