Airdrie United dumped Kilmarnock out of the CIS Insurance Cup after forcing the second round tie to penalty kicks after stalemate in normal time.
Killie had dominated throughout the game but were made to pay for their poor finishing in front of goal when the Second Division side won the clash 4-3 on penalty kicks.
Only Alan Gow missed from the spot for Airdrie as Steve Docherty, Simon Vella, Paul Harvey and Mark McGeown all netted.
But misses from Alan Mahood and Garry Hay ended Killie's run in the competition, despite successful penalty kicks from Jesus Sanjuan, Stevie Fulton and Kris Boyd.
The home side pushed forward right from the outset and could have been ahead after seven minutes.
Fulton provided the cross and that was met by Jamie Fowler just inside the 18-yard box but he fired just over the crossbar.
Killie were threatening again five minutes later - this time Hay was the provider as he tried to pick out Paul Di Giacomo at the far post but the young striker nodded just over.
Ally Mitchell's effort after 25 minutes was blocked by the Diamonds' defence and the rebound fell to Fulton - he unleashed a long, low effort which fell just inches wide of the post.
Airdrie's first real chance came on the half-hour mark when Paul Armstrong played the ball through to Andy Gow. The striker chested the ball down but, before he could pull the trigger, goalkeeper Gordon Marshall had scooped up the ball.
Killie recovered quickly from that attack when tiny hitman Jose Quitongo bulleted a shot at goal. That was charged down by the Airdrie defence and former Diamond Sanjuan tried to follow up but he sent the ball well over the crossbar.
Nerves appeared to be getting the better of Airdrie at times and none more so than after 36 minutes when Vella almost sent the ball past his own goalkeeper in an attempt to clear a Killie attack.
Kilmarnock continued to pile on the pressure after the break - and still they struggled to find the back of the net.
Fowler played the ball through to Boyd six minutes after the re-start but the teenager nodded just past the post.
Two minutes later Di Giacomo saw his long, low effort comfortably held by Airdrie goalkeeper Mark McGeown.
Desperate to break the deadlock, the two Killie hitman combined well after 56 minutes when Boyd fed the ball through to Di Giacomo and the 20-year-old should have netted - instead he fired the ball across the face of goal and just past the upright.
Killie made a claim for a penalty in the final minute of the game when Armstrong appeared to handle in the area but referee Hugh Dallas was unimpressed.
Sanjuan could have won the game with the final kick of the ball but sent the ball into the side-netting instead and the game went into extra-time and ultimately penalties.