[1] The first round draw brought Queen of the South to face Airdrieonians at the Excelsior Stadium with the home team emerging 2–1 victors.
A home game against Clydebank was the reward for reaching the quarter-finals with The Diamonds edging the opposition 4–3 on penalties following a 1–1 draw after extra time.
The second round also saw the West Lothian club drawn away from home against Ross County but produced a 3–0 win and a second consecutive clean sheet.
A first home game of the tournament for Livingston was drawn in the quarter-finals against Brechin City which saw the club produce a 3–1 win to progress to the semi-finals.
The opposition provided was East Stirlingshire, again at Almondvale and a 2–1 victory saw Livingston reach the Scottish Challenge Cup final for the first time ever.