Stenhousemuir Along with
Cowdenbeath, Stenhousemuir received a random bye into the second round. The draw in the second round saw Montrose travel to
Ochilview Park with The Warriors winning 3–1. The reward for reaching the quarter-final was an away game against Dundee at
Dens Park with Stenhousemuir producing a 3–0 victory and first
clean sheet of the tournament to progress to the semi-finals. The opposition was an away game against Stirling Albion, who had ground shared with Stenhousemuir in 1992–93. The game was played at Albion's new
Forthbank Stadium which saw Stenhousemuir win 2–1 to send the club into the Scottish Challenge Cup final for the first time in its history.
Dundee United Dundee United faced a trip to Stranraer in the first round which saw the team emerge 2–0 winners. The second round was the first and only home game of the tournament for Dundee United with the visitors in the form of Hamilton Academical with United producing a 3–0 victory at
Tannadice. A trip to Clydebank was the reward for reaching the quarter-finals with Dundee United edging the opposition out to win 1–0, in the process completing a third consecutive clean sheet. Dunfermline Athletic provided the opposition for Dundee United in the semi-finals with the team producing a 4–0 victory at
East End Park and a fourth consecutive clean sheet of the tournament. Dundee United reached the Scottish Challenge Cup final for the first time. == Pre-match ==