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Portugal were denied an automatic qualification spot at the 2022 FIFA World Cup after Serbia snatched a late winner in Lisbon on the final day.
Aleksandar Mitrovic scored a 90th-minute header to break Portuguese hearts, and the Selecao will now have to negotiate their way through the dreaded play-off round to book their place in the competition.
Renato Sanches put the hosts in front in just the second minute, but Dusan Tadic equalized for the Eagles before the break.
While it was an even game in the second period, Portugal still looked more dangerous, but failed to exert their dominance in the game and eventually paid the price.
Serbia secured their second consecutive World Cup appearance while Portugal will learn their fate on 26 November, when the draw for the play-offs will be made.
Here are the major talking points points from the game:
#5 Should Portugal's early opener have been allowed to stand?
Just like the reverse fixture back in March, the game wasn't devoid of controversy. In fact, it befell as early as the second minute when Sanches struck for Portugal.
While there was nothing wrong with his finish, the problem was in the build-up - Bernardo Silva dispossessed Nemanja Gudelj with what looked like a rough challenge.
Far from penalizing the Manchester City star, the referee allowed the match to play on, and seconds later, Portugal were in front.
How much of a foul was that? Silva's challenge on Gudelj led to a tangle of legs, with the Serbian midfielder going to the ground as a result.
#4 Night of redemption for Serbia
Almost exactly 12 months ago, Serbia lost to Scotland on penalties in the final play-off round of the Euro 2020 qualifiers and thereby missed out on a spot in the tournament.
To make things worse, they endured the heartbreak in their own backyard, just without the fans.
Now, fast-forward your calendar to the present day, and the Eagles have secured a direct route to Qatar for the 2022 World Cup by winning Group A undefeated!
What were the odds, really? Portugal had the home advantage. Serbia had never beaten Portugal in a competitive game before. Portugal also had a superior goal-difference coming into the game.
Yet, look how this has turned out to be! Football, bloody hell...
#3 Portugal pay the price for complacency
What really should've been a comfortable victory ended in a heartbreaking loss for Portugal, who now have to go through the dreaded play-off round once again to book their place at the Qatar showpiece.
Frankly, this is all their own doing. The Selecao were at home, had the goal-difference advantage, had never lost to Serbia before, and most importantly, have a squad stacked with superstars.
Yet, here we are. Following the early opener, it looked as if they were going to cruise through the rest of the match hassle-free, but Fernando Santos' side failed to finish the game off and dropped deep, allowing Serbian pressure to pile up.
While Rui Patricio could've done better for Tadic's goal, Portugal's defense switched off for Serbia's second, and Mitrovic was absolutely unmarked inside the box while placing his header into the net.
#2 Mitrovic beats Ronaldo in the battle of goalscoring talismen
The game saw two of the most prolific marksmen from Group A, Ronaldo and Mitrovic, go head-to-head once again. Given the circumstances, it was always going to boil down to them to produce late heroics.
But few would've bet on Mitrovic to do that over Ronaldo, who had a quiet night instead.
The Fulham striker snuck in behind the Portuguese defense to head in a fine whipped cross from Tadic from close range, stunning the mighty home side.
That was his eighth goal of the qualifying campaign, two more than his Manchester United counterpart, who drew a blank in consecutive games.
#1 Is this the World Cup without Ronaldo?
All is not yet lost for Portugal, despite the loss. They're still very much in the race to qualify for the 2022 World Cup, but it only gets tougher from here.
The play-offs are a one-legged affair, so there's virtually no room for error, and as Serbia showed last night, nothing is ever a guarantee.
The Selecao might as well be the most decorated side in the round, but they will face some tough opposition.
Sweden, North Macedonia, Wales, Scotland and Russia have booked their place in the play-offs, while one of Italy and Switzerland will also be joining them.
Portugal qualified for the 2010 and 2014 World Cups only after winning in the play-offs, but it has become more competitive than ever before since then.
The Qatar showpiece is also likely to be the final international swansong for Ronaldo, who'll be almost 38 by the time it comes around.
But now, thanks to Portugal's disappointing campaign, he risks missing out on a spot in the competition altogether.
Can he step up and drag his team to the finals again?
