The Republic of Ireland, Northern Ireland and Scotland were all looking to take huge steps towards Euro 2020 qualification on Thursday night.
Ireland looked to keep their hopes of qualifying for the tournament alive in a difficult trip to Slovakia.
Ian Baraclough's Northern Ireland, meanwhile, travelled to the Grbavica Stadium to take on Bosnia & Herzegovina.
And Steve Clarke's Scotland welcomed Israel to Hampden Park, where they hoped to make the most of home advantage to book a place in the next round of the play-offs.
Unlike the play-offs we've become accustomed to seeing down the years, tonight's fixtures were a one-off due to the ongoing coronavirus pandemic- meaning the losing side would be immediately eliminated after the final whistle.
Here's how an eventful night unfolded…
Euro 2020 play-offs round up
Republic of Ireland suffer penalty shootout heartache
The Republic of Ireland won't be gracing the next European championships.
After being held to a goalless draw, Stephen Kenny's men were eliminated via the dreaded penalty shootout – which they lost 4-2.
The visitors got off to a good start at the National Football Stadium, imposing themselves early and having the lion's share of possession.
Preston North End's Alan Browne had the best chance in the 70th minute but was unable to find a way past Marek Rodak, who made a fine save at his near post.
Ireland continued to pour on the pressure but were unable to breach the resilient Slovakian defence in normal or extra time.
And they were made to rue their missed opportunities as shootout misses from Browne and Tottenham new-boy Matt Doherty saw them miss out on the chance to play in next year's tournament.
Had The Boys in Green won tonight, they would've set up a tasty Battle of Ireland against their counterparts in the north. Alas, it wasn't to be.
Northern Ireland win shootout to set up Slovakia tie
In stark contrast to their southern neighbours, Northern Ireland experienced the ecstasy that comes with winning the feared penalty shootout.
After being held to a 1-1 draw, Baraclough's troop's triumphed 4-3 in the shootout.
They got off to the worst possible start at the Grbavica Stadium, falling behind to a 13th-minute goal from AC Milan midfielder Rade Krunic.
Baraclough's men didn't let their heads drop, huffing and puffing to try and find an equaliser.
And they were rewarded for their efforts in the 53rd minute when Aberdeen's Niall McGinn capitalised on some lax defending to fire them level with a tidy finish from just inside the 18-yard-box.
The visitors continued to pile on the pressure and came agonizingly close to claiming victory in the 80th minute when Gavin Whyte's deflected shot went narrowly wide of the post.
The tide, however, began to turn in the first period of extra time – with keeper Bailey Peacock-Farrell being called upon twice.
Bosnia maintained their dominance throughout extra time but were unable to find a way past Peacock-Farrell, meaning the contest went to the dreaded penalty shootout.
Consecutive misses from Haris Hajradinovic and Edin Visca cost the home side, who were sent packing courtesy of a successful spot-kick from Liam Boyce.
Scotland edge shootout to set up Serbia showdown
Scotland's hopes of qualifying for their first tournament since France '98 rested on them avoiding defeat at Hampden Park.
And they took a giant step towards their long-overdue return to the international stage thanks to a 5-4 penalty shootout victory – which came after a tense 0-0 draw.
Manchester United's Scott McTominay came close to giving the hosts the lead moments before the half-time with a header that went narrowly.
Steve Clarke's men dominated the majority of the second-half but were unable to find a way past the resolute Israeli defence, which withstood wave after wave of Scottish attack.
The Israeli's held firm in extra time, but they were sent crashing out thanks to a top-drawer save from David Marshall to deny Eran Zahavi in the shootout – which booked the Scots a place in the play-off final against Serbia.
Clarke may be over the moon with the result, but even he knows his side will have to play a lot better than they did tonight if they're to have any chance of getting the better of the Serbs.
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