Stenhousemuir kept alive their hopes of repeating their shock Challenge Cup win of nearly 20 years ago with a sparkling second-half showing to stun 2014 champions Raith.
This Petrofac Cup tie was an intriguing battle of two former Challenge Cup winners, Stenny in 1995-96 and Raith much more recently against Rangers.
Ray McKinnon’s Raith made the brighter start in the sunshine at Ochilview with a few decent efforts in the early stages.
Ryan McCord volleyed wide from the edge of the box before Craig Wighton latched on to Mitch Megginson’s cross but Jamie Barclay saved.
Stenny started to get a foothold and on 21 minutes Jon McShane smashed a 12-yard shot off the bar after Alan Smith’s flick-on.
The Warriors had momentum and on the half-hour Kevin Cuthbert did well to push away Stuart Malcolm’s header.
Two minutes after the break Alan Smith almost had the Warriors in front with a snapshot but Cuthbert made a fine one-handed save.
McShane sent a looping header just over Cuthbert’s crossbar on 61 minutes after am enticing cross from full-back Jamie McCormack on the overlap.
This was anybody’s game with both sides probing for the opener. However, it would need something special to break the deadlock.
Alan Cook duly delivered with a perfectly placed left footed finish from the left of the box drilled into the bottom right after McShane’s assist.
Raith were so close to an equaliser on 70 minutes with on-loan Dundee man Wighton heading off the post.
They were to rue that miss less than 60 seconds later when Stirling caught Cuthbert off his line with an audacious 25-yard lob.
Raith skipper Jason Thomson was shown a stoppage-time red card for a late tackle on Stirling.