The Spurs striker had the chance to force extra time at the Al Bayt Stadium but France triumphed 2-1 thanks to his horrific miss.
It may not have been a shootout but it was still the same old story for England: more penalty pain.
What was remarkable about the Three Lions' latest spot-kick sorrow was that Harry Kane had actually converted one to level this enthralling World Cup quarter-final at the Al Bayt Stadium.
However, when the Spurs striker was given the chance to restore parity a second time after Olivier Giroud had headed France into a 2-1 lead, Kane ballooned the ball over the bar, evoking memories of Chris Waddle at Italia '90.
This latest failure from 12 yards out will arguably hit even harder than that infamous loss to West Germany. England had been the better side after falling behind to Aurelien Tchouameni's stunning early strike from distance.
However, after Kane had seemingly broken the curse to join Wayne Rooney on 53 goals for England, it struck again with just six minutes of normal time remaining to leave a nation dealing with an all-too-familiar feeling of devastation.
Below, GOAL runs through all of the winners and losers from a bittersweet night for Kane in Al Khor.
Winner: Antoine Griezmann
If this World Cup has proven nothing else, it's that Antoine Griezmann is an extraordinary footballer. It really is as simple as that. The former forward has reinvented himself as France's hybrid hero, an incredibly effective link-man between the attack and the midfield. England fans may disagree given his penchant for making tactical fouls, which earned him a yellow card, but Griezmann was the best player on the pitch at the Al Bayt.
His pass accuracy during the first half was 96 per cent – an extraordinary success rate for a player playing in an offensive position. What was even more impressive was the fact that he didn't misplace a single pass in the final third during those opening 45 minutes, and one of those balls ended up at the feet of Tchouameni, who opened the scoring with a sweet strike from distance.
Then, just as he had done against Denmark, Griezmann created a winning goal at a time when his side were struggling, this time picking out Giroud with a fantastic delivery from the left wing with that wonderful left foot. Still no goals for Griezmann at Qatar 2022 but that's no longer relevant. He's firmly established himself as France's most influential player.
Loser: Harry Kane
On the eve of the game, Hugo Lloris was asked about the prospect of facing a Harry Kane penalty. It was suggested that he might benefit from a little inside knowledge, given he's squared off with the England striker in countless Tottenham training sessions. Lloris replied, "You know better than me that Harry has the ability to shoot anywhere.
He's one of the best probably at this aspect of the game." Kane proved Lloris' point nine minutes into the second half, sending his Spurs team-mate the wrong way with an emphatic spot-kick to level the game. Mbappe had even tried to offer Lloris a word of advice – or perhaps, more accurately, psyche out Kane – but the No.9 would not be denied what was fourth consecutive successful penalty attempt at the World Cup.
And, far more significantly, his record-equalling 53rd goal for England. However, when Kane was once again called upon with just six minutes of normal time remaining, he cleared the crossbar with an atrocious attempt. From history to horror in just half an hour for the England skipper.
Winner: Olivier Giroud
Olivier Giroud was having a pretty horrid evening. His team may have been leading at the break but their No.9 had managed just seven touches in the opening 45 minutes. Then, when a big chance finally came his way in the final quarter of the game, he volleyed an Ousmane Dembele knockdown far too close to Jordan Pickford.
However, Giroud, who didn't play top-flight football until he was 24, didn't make it to the pinnacle of his profession by allowing his head to drop. If at first, you don't succeed and all that.
Just moments after squandering a gilt-edged opportunity, Giroud cleverly moved in between England's two centre-halves to head home. It was fantastic centre-forward play and showed precisely why the 36-year-old is his nation's all-time record goalscorer. As he said himself afterward, scoring a historic 52nd goal for France felt great, but his 53rd was even better. It's time to put a serious amount of respect of Olivier Giroud's name.
Loser: Theo Hernandez
The luckiest man at the Al Bayt. France had just regained the lead. They were trying to kill the game yet their left-back gifted England a way back into it. There was absolutely no need for Theo to even touch Mason Mount as he hopefully chased a punt into the France area.
The England sub wasn't going to get anywhere near the ball. Why on earth, then, did Theo feel compelled to clatter into Mount? Was it a show of machismo? Was he trying to prove a point? All we know for sure is that it was as unnecessary as it was stupid. Honestly, Hernandez didn't deserve to be let off the hook by Kane for the most idiotic of challenges.
He remains an outstanding attacking full-back but he clearly still has a lot to learn about disciplined defending.
Loser: England's best shot since 66
Football isn't coming home. But Gareth Southgate and his players are. There will be regrets and recriminations. It will be pointed out that England didn't claim one major scalp at Qatar 2022; that their record against the big boys remains distinctly unimpressive.
There is, of course, zero shame in losing to this France team at the quarter-final stage. They are defending champions after all. What's more, while Didier Deschamps' squad was rocked by the withdrawal of several superstars before the tournament began, their starting line-up is still stacked with world-class players.
And yet, England were the better side after Tchouameni's thunderbolt. This game was there for the taking and, at the very least, they should have forced extra-time. Indeed, it's impossible not to view this in the same way as Kane's second spot-kick – as a painful missed opportunity. Remember, only Morocco would have been left standing between England and a place in a first World Cup final since 1966.
Spain and Portugal have already paid a heavy price for underestimating the Atlas Lions but Africa's history-makers could be running on empty by next Wednesday's semi-final. France are now the overwhelming favourites to win this World Cup. England are perfectly entitled to feel it should have been them – and that's only going to make this defeat all the more difficult to take.
Their young players are only going to improve. They will be serious contenders at Euro 2024. However, as Kane admitted beforehand, an inexperienced group of over-achievers had just enjoyed the ride in Russia 2018, whereas the current crop of world-class players had actually arrived in Qatar believing they could win the tournament outright.
In that context, then, a quarter-final elimination cannot be portrayed as anything other than a massive disappointment. Some of these players should get another chance to win the World Cup, but they'll never get a better one.