Portugal had qualification in their hands on Sunday night as they hosted Serbia.
A draw would have been enough to seal top spot in Group A.
And they got off to the best possible start when Renato Sanches gave them a second-minute lead.
However, that was about as good as it got on the night for Fernando Santos’ side.
By half-time, it was 1-1 as Dusan Tadic equalised.
The ultimate Cristiano Ronaldo quiz
It was tense after the break. No side wanted to make a mistake that could cost them an automatic place at the World Cup.
That was until Aleksandar Mitrovic popped up in the last minute of normal time with a dramatic winner.
VIDEO: Mitrovic's winner for Serbia vs Portugal
Serbia were through and Portugal must now go through the lottery of the playoffs.
At full-time, many Portugal players were in disbelief as they struggled to comprehend they had thrown away top spot.
Ronaldo was probably the most animated.
At full-time, the Manchester United man was seen gesticulating wildly towards his manager.
VIDEO: Ronaldo was fuming at full-time
What was he saying?
Well, after the match, Santos said: "He was saying to another player that there [in Serbia] he scored a last minute goal that the referee didn't allow. His outburst, it's normal, he was frustrated."
Ronaldo remembered his 'goal' vs Serbia
And if you can’t quite remember that disallowed goal, let us remind you…
In the fixture between the two sides in Serbia, Ronaldo appeared to score an injury-time winner with the scores at 2-2. Replays showed the ball had clearly crossed the line but, with no goalline technology in place, the goal wasn’t given.
Ronaldo responded angrily before walking off the pitch and chucking his captain’s armband away in disgust.
VIDEO: Ronaldo's 'goal' vs Serbia that didn't count
If that goal had counted as it should, Portugal would have qualified for the World Cup and Serbia would be in the playoffs.
Ronaldo now needs to channel his anger and produce yet another clutch moment to play in his final World Cup finals in Qatar.News Now - Sport News