Portugal have suffered a shock home defeat at home to Serbia.
The winner of the game stood to seal World Cup qualification for 2022, and a draw would have been enough for Portugal.
Portugal had a dream start, going 1-0 up in the fourth minute through Renato Sanches.
But Serbia fought back, equalising in the first half through Dusan Tadic.
Aleksandr Mitrovic then scored an injury time goal for Serbia to stun the home crowd.
Serbia have now qualified for the World Cup and Portugal must go through the play-offs.
A disaster for Ronaldo
Ronaldo was hoping the 2022 World Cup could be his crowning achievement, the one trophy missing from his collection.
Now there is a real chance he may not even be at the tournament.
Portugal will go into the play-offs and have to win two matches against different opponents to qualify.
Ronaldo played all 90 minutes of the defeat to Serbia.
Bruno Fernandes started the game on the bench and came on in the second half, while Diogo Dalot was an unused substitute.
This adds more misery for Ronaldo and Fernandes, who have endured a very testing start to the season for Manchester United, with the side desperately out of form.
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