Goalkeeper Chris Maxwell was the shoot-out hero as Hibernian booked their place in the Betfred Cup semi-finals after beating Kilmarnock on penalties at Rugby Park.
A cagey first period yielded few chances and, while there was a noticeable improvement in the second period, neither team could break the deadlock inside 90 minutes and extra time was required.
Hibs were reduced to 10 men in the 120th minute when Ryan Porteous was given his marching orders and the tie had to be decided by a shoot-out after the extra period finished goalless.
The shoot-out was decided when Niko Hamalainen’s penalty was saved by Maxwell, handing Hibs a 5-4 victory.
The first half got off to a scrappy start, with a series of minor fouls disrupting the flow of the game.
The hosts won an early corner when Stephen O’Donnell’s ball into the box had to be beaten behind by visiting goalkeeper Maxwell. But it came to nothing as an acrobatic shot from the middle of the box sailed wide.
The game’s first meaningful chance came in the 25th minute when Hibs midfielder Stevie Mallan sent a low shot wide from just outside the area.
Hibs midfielder Melker Hallberg completely missed the target from 35 yards before two good balls into the home box were expertly dealt with by Kilmarnock’s defence.
The visitors continued to ask questions of the home side as the first half wore on but came no closer to opening the scoring as Christian Doidge failed to connect with Lewis Stevenson’s cross in the 35th minute.
Stuart Findlay had a header nodded behind by Porteous in the closing stages of the half, just after Killie had another penalty appeal waved away.
Hibs started the second half strongly and only some last-ditch defending prevented Josh Vela from shooting at goal as the ball became loose in the box in the 47th minute.
Harvey St Clair swung in a fierce cross in the 53rd minute which gave Maxwell a fright before grazing the bar, but it evaded everyone in the box and bounced to safety.
Hibernian forward Glenn Middleton had the ball in the net in the 62nd minute but the linesman’s flag was already up.
The away side came close again 10 minutes later as substitute Shaw’s header was tipped over by home goalkeeper Laurentiu Branescu.
Killie had a golden opportunity to open the scoring in the 79th minute when Eamonn Brophy found himself with space to run into 30 yards from goal and visiting goalkeeper Maxwell slipped to the floor in the box.
But Brophy rushed his shot and fired harmlessly over the bar.
O’Donnell sent a dangerous ball into the box as Killie pushed forward in stoppage time but Maxwell was equal to it.
Some neat build-up play from Doidge presented Shaw with a good chance in the 96th minute but the substitute sent his effort wide from the edge of the box.
Dominic Thomas came close for the home side in the 107th minute, racing down the right wing and delivering a fine cross which struck the bar.
The visitors were reduced to 10 men late on when Porteous was shown a straight red card for bringing down substitute Liam Millar.
Killie won the shoot-out when Maxwell guessed the right way to keep out Hamalainen’s effort.