Kilmarnock 3 St Mirren 3 (St Mirren won 5-4 on penalties)
Kilmarnock were left heartbroken as their first trip to Hampden since 2012 was taken away from them in the cruellest fashion.
Saints took an early lead thanks to Ilkay Durmus but Zeno Ibsen Rossi and Greg Kiltie ensured the hosts went into half-time ahead.
Joe Shaughnessy was the Buddies hero with seven minutes to go as he headed the tie into extra-time.
Killie were forced to play the final 25 minutes with 10 men when Nicke Kabamba was taken off due to injury and Killie had used all of their substitutes.
But a Ross Millen penalty was enough to give Killie the lead that left Saints gutted.
However, Jamie McGrath fired home his spot-kick in the 119th minute to send it to a shoot-out in which St Mirren scored every one.
The visitors had the first chance just three minutes in when former Killie hitman Lee Erwin’s cross fizzed across the goal but it was missed by Kristian Dennis and Durmus.
Mitch Pinnock carried the ball into the box from the wing for the hosts but his wild shot went well over the bar, leaving keeper Jak Alnwick worry-free.
Saints youngster Jay Henderson went close in the 13th minute when he latched on to a cross but his effort was well blocked.
Kiltie tried his luck from distance in the 19th minute with a powerful effort but he couldn’t quite direct it on target as it fell wide of the post.
It took 24 minutes for the deadlock to be broken and it came via the visitors who took the lead thanks to Durmus after his shot was fumbled in by Killie keeper Colin Doyle.
Saints looked sure to score again four minutes later when they were through on goal but Killie were let off the hook thanks to the offside flag.
The hosts appealed for a penalty when George Oakley appeared to be hauled down in the box but the protests were quickly waved away.
In the 36th minute, the scores were back to even when Rossi fired home a header from a Chris Burke corner.
Just before half-time, the hosts took the lead thanks to Kiltie who fired in off the post after a cutback from Oakley.
Killie had penalty shouts waved away for a second time two minutes into the second half when Kiltie was tackled in the box, but play was waved on after Shaughnessy’s challenge.
In the 52nd minute, the hosts looked sure to take the lead when Millen headed towards goal, but his effort was blocked off the line by McGrath.
Kiltie had another chance just before the hour mark when he fired a shot from the edge of the box on target, but it was well saved by Alnwick who tipped it round out for a corner.
Kirk Broadfoot fired a header towards goal from the resulting set-piece but it was well saved.
In the 72nd minute, Oakley tried to flick an effort home from close range but his effort went narrowly over the crossbar.
Richard Tait fired a cross to Marcus Fraser three minutes later but the defender’s header went straight at Doyle.
Conor McCarthy was booked with 10 minutes to go for a rash challenge on Pinnock just outside the box but the resulting free-kick led to nothing.
In the 83rd minute, Shaughnessy popped up from a set-piece to head home and bring the visitors level.
Saints looked sure to score in the 89th minute when Collin Quaner had a close-range shot but it was well saved by Doyle and Fraser then headed the rebound wide.
Kabamba worked his way through on goal a minute into extra-time, but he dragged his shot wide.
The striker was then taken off due to injury forcing Killie to play with 10 men for the rest of extra-time.
But that didn't stop them as they took the lead in the 101st minute thanks to a Millen penalty.
But with a minute to go Saints equalised thanks to a penalty of their own and they converted thanks to McGrath.
It was then on to the shoot-out with Rory McKenzie's effort saved by Alnwick the decisive moment as the Buddies made no mistake with their five efforts to set-up a semi-final clash with St Johnstone.
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