Arsenal bowed out of the Europa League after losing 5-4 on penalties to Sporting Lisbon, after an utterly thrilling second leg of their last 16 tie at the Emirates Stadium finished 1-1 after extra time.
With the scores level at 2-2 after last week's first leg, this one looked up for grabs – and Sporting seized the opportunity with both hands on a pulsating night in North London.
While it could ultimately be a blessing in disguise for the Premier League leaders, this was the Gunners' earliest exit from continental competition since 1999 – and it had all started so well for Mikel Arteta's side.
Granit Xhaka, starting as captain with Martin Odegaard on the bench, opened the scoring 19 minutes in, capping a slick counter-attack by smashing in the rebound after Gabriel Martinelli's initial effort was well saved by Antonio Adan.
After failing to capitalise on some sloppiness from the hosts, Sporting eventually equalised with one of the most incredible goals you'll see anywhere this season.
Having received the ball just inside his own half following an Arsenal mix-up, Pedro Goncalves looked up to see Aaron Ramsdale off his line and quite outrageously lobbed the back-peddling Gunners goalkeeper from the edge of the centre circle.
The goal might well have sparked flashbacks among the home fans to the 1995 Cup Winners' Cup final, where Real Zaragoza's Nayim bamboozled David Seaman in similar fashion to break Arsenal hearts in the last minute of extra time.
Ramsdale appeared unperturbed by Goncalves' Puskas Award contender, though, keeping Arsenal in it by denying Marcus Edwards with his face from point-blank range just minutes later – a save which ultimately took the tie to extra time.
Leandro Trossard came closest to winning it in extra time, seeing his shot midway through the first period brilliantly touched onto the post by Adan after a horribly misplaced pass by Youssef Chemiti.
And Adan – who had a fantastic first leg in Lisbon – was to prove the hero yet again in the closing minutes, denying Gabriel by keeping out the defender's headers from a free-kick then a corner in quick succession.
With the game heading for penalties, Sporting were reduced to 10 men as Manuel Ugarte picked up a second yellow for a reckless challenge on Bukayo Saka.
And so to spot-kicks this captivating contest went – and Arsenal's first home shootout in 20 years.
Taking first at the end of the ground where their raucous travelling support were situated, Sporting may have sensed some sort of advantage – and so it proved.
After Martinelli's poorly struck penalty had been kept out by the consistently heroic Adan, Nuno Santos buried the decisive kick to send the visitors through.
For Arsenal, now out of all three cup competitions, it's all about continuing their push for a first Premier League title since 2004 – beginning with a London derby at home to Crystal Palace on Sunday.
