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Argentina are facing the prospect of an early World Cup exit after a dreadful error from goalkeeper Willy Caballero set Croatia on their way to victory and a place in the last 16.
On a night when so much was expected of Argentina captain Lionel Messi, Caballero made the most telling contribution to his team's fate with an attempted chip over Ante Rebic that backfired badly, allowing the striker to volley into an exposed net in the 53rd minute.
Messi - adrift for much of the match, especially during a pedestrian opening half - rallied his side, but neither he nor substitute forwards Gonzalo Higuain and Pablo Dybala could find a way through in Nizhny Novgorod.
The closest Messi came was a half-chance, a snatch at a rebound from a Maximiliano Meza shot which was blocked by Ivan Rakitic and turned behind to safety.
It was a dogged defensive second-half display from Croatia, illuminated by a moment of magic from their own masterful number 10, Luka Modric.
His curled shot from range drifted beautifully beyond Caballero's dive to put his side two ahead, before Rakitic's injury-time tap-in sealed a victory that moves the Europeans through to the knockout stage and also leaves them in a strong position to win the group.
Argentina are no longer in control of their own destiny. This defeat follows their opening 1-1 draw with Iceland, in which Messi missed a penalty, and now even a heavy win over Nigeria in their final game on Tuesday may not be enough to send them through to the next round.
Should Iceland beat Nigeria in their second Group D game on Friday, Iceland would need only a draw against Croatia in their final match.
For Messi, a prolific performer at club level with Barcelona, this was another harrowing chapter in his recent history of pain and disappointment in the international game.
As the national anthem was played before the match, the camera panned across Messi's face. Eyes closed as he rubbed his forehead, he looked like a man carrying the expectations of a nation.
He wanted to perform too, to carry his team in the shape of his own greatness like the legacy of Diego Maradona says he must, but this was a long way from a classic Messi display. This is also a long way from a classic Argentina team.
In the first half they were easily exposed on the flanks, conceding three first-half chances behind the full-backs which a more ruthless side than Croatia would have punished.
At the other end, Enzo Perez missed a sitter and looked out of depth in midfield, while Messi was often wandering in empty space with the game played somewhere else.
It was a strange thing to watch, to see the player who is so often nothing less than masterful at the highest level of the club game not stepping forward into the spotlight.
There seems to be real tension - a barrier almost - to success in the blue and white stripes of Argentina.
It has become more pronounced and painful over the past four years, during which Argentina lost three major finals with Messi as captain.
After the most recent of these - defeat by Chile in the 2016 Copa America - Messi announced his international retirement, having missed a penalty in the shootout.
He reversed the decision a month later but now, three days before he turns 31, you feel this really was the last big chance he had of propelling his side to victory on the biggest stage of all.
Even if international success does not come - and it looks a long way off - he will still be the player who has achieved so much and seduced so many in 14 years at Barcelona.
But at a tournament where Cristiano Ronaldo is again dragging Portugal along with his goals and drive, there will forever be regret and a sadness that a player as talented as Messi looks likely to have one thing missing: a World Cup he defined.
Until Argentina crumbled late on, Croatia had not been particularly impressive either.
Although they probably edged the quality of chances created, they were all chances wasted. Ivan Perisic had a low drive brilliantly tipped round the post, Mario Mandzukic put a low header wide from six yards, and Rebic blazed wastefully over from a wondrous Modric through ball.
There were few signs to suggest Croatia would end up winning as convincingly as they did as Argentina enjoyed the majority of possession and almost scored a freakish opener when Meza hit the top of the bar with a cross.
Later, Croatia produced moments of real quality such as Modric's sumptuous curled finish and the composed passing before Rakitic's third. But those came after the defining action of the night - Caballero's mistake.
He is only covering Manchester United's Sergio Romero, who was ruled out before the tournament through injury.
It was the kind of error nightmares are made of, and it seemed to strike a blow at the heart of the morale of the Argentina team.
So many heads, including Messi's, dropped in bemusement and misery. From that point on, it only got worse for them.
The Real Madrid midfielder scored a superb goal and had 62 touches, making 29 passes in the opposition half - the most by a Croatia player - with an accuracy of 82.8%
Argentina coach Jorge Sampaoli: "First and foremost I beg for the fans' forgiveness. The reality of the Argentina squad clouds Lionel Messi's brillance. The team doesn't gel as well as it should.
"I have always looked for the best position on the pitch for my players. The players have a special responsibility as well, but we didn't manage to find relationships that Argentina or Lionel Messi benefited from.
"Croatia were an excellent team, but after we conceded we lost our way and we were emotionally broken. We couldn't change the course of events.
"I am very hurt by the defeat but I probably didn't understand the match as I should have."
Croatia coach Zlatko Dalic: "I have trusted my team from the first day. I didn't believe we would be through after the second game so we have to be happy because we have beaten a strong Argentinian side with the best player in the world. Argentina were not confused; we were excellent.
"Over the last few days we haven't looked at tactics because I wanted to relieve my players of the stress. We had good scouts and we analysed the opposition well. We adapted our style to them. Let's enjoy this moment.
"In the first half we were compact and created three sitters but we failed to score. That's why I told the players in the second half that we will create more chances but we had to press higher."
