Dundee Utd0–0Airdrie

United gave home debuts to Wright, Tchami and McDonald.

There was plenty of apetite from both sides early on but composure in the final third was lacking. The first notable incident came when Jim Paterson was stretchered off and Stephen Thompson came on as a substitute. David Fernandez went close on 20 minutes with Stephen Wright forced to clear.
In 31 minutes Barry Elliot's cross was just missed by Fernandez while Aljofree was off the pitch receiving treatment. Airdrie went close again after 44 minutes when McCann's cross was cleared by David Partridge. Jamie Buchan forced Broto into a 46th minute save with a 35 metre shot in the last action of the half.

United appeared for the second half with David Hannah on for Neil Heaney as Alex Smith elected to play a 4-3-3 formation. Airdrie came close in 47 minutes when Elliot's cross was again missed by Fernandez. Hannah's free kick is well saved by Broto who turned the drive over for a corner before in 67 minutes a teasing Buchan cross is just missed by Thompson. John Elliott was through on goal in 69 minutes but Alan Combe saved well. United switched to a 3-4-3 formation as they looked to avoid the game going to extra time and the chances were increased late on when Fernandez was sent off following an incident with De Vos. Tchami shot wide in injury time after fine work by Hannah in what proved to be the final chance of normal time.

The hosts pushed forward in extra time and Hannah's 35 yarder in 97 minutes was spectacularly saved by Broto for a corner. Buchan's kick is then headed wide by Tchami. Airdrie sub Pacifico then brought out a fine save from Combe in 99 minutes with a 20 yard shot. United were enjoying all the possession but couldn't break down a stubborn Airdrie defence. With 2 minutes of extra time to play Aljofree had a chance but struck weakly at Broto meaning it was going to take penalties to settle the contest.

Airdrie took the first kick which Sanjuan scored. Thompson made no mistake in reply for United to level at 1-1. McCann then put the Diamonds 2-1 ahead and when Tchami's penalty struck the bar, the signs didn't look too good for the Terrors, especially after Moreau scored to make it 3-1 for Airdrie. Wright netted for United and then Calderon's kick was superbly saved by Combe giving the Tangerines the opportunity to get back on level terms. When Hannah powered home his penalty into the roof of the net the match was levelled at 3-3. Combe then saved from Forrest leaving De Vos has the chance to win a quarter final berth for the home side. Thankfully he made no mistake and the Tangerines breathed a sigh of relief as they celebrated a 4-3 shoot-out win.