Under-pressure Rangers boss Ally McCoist suffered yet more humiliation in the Petrofac Training Cup as Alloa denied them a place in the final with a stunning 3-2 win at the Indodrill Stadium.
The Ibrox manager was already facing stick from his own support after falling nine points behind promotion rivals Hearts in the Championship.
But his position will come under fresh scrutiny after his side blew a two-goal lead against Barry Smith's minnows before crashing out to Grieg Spence's last-gasp winner.
Kenny Miller and Dean Shiels put them ahead early in the second half, but two goals in three minutes from Spence and Ryan McCord fired Alloa back into the game.
Jon Daly was denied what looked like a certain goal by a stunning reflex save from home goalkeeper Craig McDowall but it was Spence who ensured Alloa would be the side taking on Livingston on April 5 at a venue yet to be announced.
But whether McCoist remains in charge until then remains to be seen after the Light Blues lost to Alloa for the first time in any competition.
His side have now bowed out of the lower-league cup contest three seasons running.
Last year's defeat to Raith Rovers in the Easter Road final heaped shame on the manager but losing to Smith's part-time outfit is undoubtedly the worst result of his three-and-a-half year reign.
The Ibrox side had looked strong as they knocked Kilmarnock out of the William Hill Scottish Cup on Sunday but they lacked any cohesion as they kicked-off in Clackmannanshire.
Losing midfielder Lewis Macleod early did not help their cause. The Scotland Under-21 youngster was hurt on Alloa's plastic pitch on his last visit back in September and suffered a repeat as tumbled to the ground clutching his ankle after just 10 minutes.
McCoist looked worried as he sent for Shiels while his talented playmaker was carried off on a stretcher.
The boss' concerns did not lessen as his side continued to struggle. They switched off at a free-kick but were lucky Spence could not connect properly with the loose ball.
Adam Ashgar then came close as he bulleted a shot from 25 yards out, but Liam Buchanan should have scored from closer range after Lee McCulloch held up Spence.
The visitors had come nowhere near testing McDowall in the first half but within four minutes of the restart were ahead.
Kris Boyd registered their first shot on target with a 25-yard free-kick but McDowall could only push it back into traffic. Miller, though, was well-placed to gobble up the rebound.
McDowall did get a hand to Darren McGregor's strike but Bilel Mohsni nearly handed Alloa a leveller when he diverted Buchanan's cut-back towards his own net. Steve Simonsen, though, dug him out of a hole with a reflex stop.
Rangers wanted a penalty after 62 minutes as Ben Gordon appeared to handle Fraser Aird's shot but referee John McKendrick waved away their demands.
Within two minutes, though, Shiels had Gers' two-up. After collecting a pass for Miller inside the box, the Northern Irishman kept a calm head as he cut past his marker before sliding a tidy finish into the bottom corner.
The Light Blues should have been cruising but they allowed Alloa a lifeline on 72 minutes as Spence headed home from Mark Docherty's cross.
And they were still sleeping three minutes later as Edward Ferns sent a low ball across their six-yard box for McCord to finish off.
McDowall kept Alloa in it with a point-blank range save from substitute Daly, setting up Spence to make himself the Alloa hero as he slotted home a fine finish from Steven Hetherington's pass in the final minute.
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