In the end it was really was a night that had it all as the six BetMcLean Cup second round ties produced derby victories, upsets, extra-time winners and one of the longest penalty shoot-outs in the history of the game.
Holders Linfield continued their defence of the trophy with a 2-1 defeat of great rivals Glentoran at the BetMcLean Oval.
Joel Cooper bagged both goals for the Blues, opening the scoring after a quarter-of-an-hour before doubling up early in the second half.
Jay Donnelly pulled one back for the Glens late on whilst strike partner Junior Uzokwe hit the woodwork in stoppage time but there was no stopping the Blues going through.
But all the headlines will be focused on the other derby of the evening at the Ballymena Showgrounds as Oran Kearney’s Coleraine edged past the Sky Blues after an epic 18-17 penalty shoot-out victory!
Scot Whiteside had handed United the lead just before the break, with Josh Carson levelling from the spot – ironically enough – around the hour mark.
The sides couldn’t be separated after normal or extra-time, with the inevitably of penalties needed to settle the tie.
However no-one could have anticipated the drama that was to follow with both sets of players eventually having to take two spot-kicks each before Lee Lynch settled it with what turned out to be the winning penalty.
Spot-kicks were also required at the Loughview Leisure Arena as Newry City emerged 3-1 winners over Carrick Rangers.
Ciaran O’Connor opened the scoring on 18 minutes for the visitors with yet another penalty before Kyle Cherry levelled on the hour for Carrick.
Extra-time saw Reece Glendinning momentarily tip the balance in Carrick’s favour, with Adam Salley equalising soon after.
Newry then proved to be clinical from the spot with Georgie Poynton, Thomas Lockhart and Salley all finding the net with only David Cushley registering for Carrick as the visitors went through to the next stage.
Portadown produced the upset of the evening with a 2-1 defeat of Crusaders at Shamrock Park.
The Ports moved in front after just 11 minutes when, following a mix-up in the Crues defence, Kenneth Kane found himself through on goal and made no mistake from close range.
However Mikhail Kennedy levelled for the visitors midway through the first half after slotting home from the edge of the box after Aaron Hogg had come off his line to try to win the ball from Lloyd Anderson.
But Eamon Fyfe knocked home the winner for the Championship side midway through the second half with a cool finish through Jonny Tuffey’s legs.
And there was almost an even bigger upset at Clandeboye Park as Ards took league champions Larne to extra-time before losing out in an eight-goal thriller.
Callum Dougan, Ross Hunter and Connor Maxwell all found the net for Ards with Sean Graham, Andy Ryan and Paul O’Neill responding for the visitors … but it was extra-time goals from Lee Bonis and O’Neill again that ultimately settled it in favour of Tiernan Lynch’s side.
Meanwhile, at Stangmore Park, Matthew Lusty hit the only goal of the game as Dungannon Swifts knocked out Cliftonville.
Lusty struck on 77 minutes after evading challenges from Luke Kenny and Shea Kearney to slot the ball past Nathan Gartside at the near post.
The Limavady United-Glenavon game was the subject of a late postponement following floodlight issues at the Showgrounds. A new date will be confirmed in due course.