Alloa2–3Inverness CT

Despite early Alloa goals Caley Thistle fought back to gain a late victory. Ross Hamilton took a pass from Mark Wilson then lobbed Les Fridge in a record 54 seconds to give Alloa the lead. Five minutes later Wilson crossed and Hamilton made it 2-0 with a powerful scissors-kick. Caley Thistle came back into the match and Barry Robson shot wide in 20 minutes. Alloa claimed a penalty on the half hour mark when Stuart Golabek collided with Hamilton but nothing was given. Caley Thistle pulled one back in 53 minutes when Roy McBain's fine through ball was collected by Iain Stewart and he fired home. Fridge saved from Wood two minutes later and Derek Clark cleared off the Alloa line in 63 minutes from a Ross Tokely header. The deserved equaliser came eight minutes from time when substitute David Hind crossed from the right for Stewart to head his second goal. Further pressure led to Caley Thistle's Martin Bavidge grabbing the winner with five minutes left after being set up by their other substitute Charlie Christie. Stranraer now await in round two.