A nine-man Liverpool team lost their 17-game unbeaten Premier League record in the cruellest of circumstances as Tottenham Hotspur overcame the Reds 2-1 in North London.
Cody Gakpo's leveller on the stroke of half time cancelled out a Son Heung-min opener, and the Dutchman's strike would seemingly be enough to clinch a point for Jurgen Klopp's side, who had both of Diogo Jota and Curtis Jones sent off either side of the break.
However, with the final attack of the game, Joel Matip turned Pedro Porro's cross into his own net to gift Ange Postecoglou's side all three points after a truly chaotic capital contest.
There was no shortage of intensity from either team during a frenetic opening, one which saw Alexis Mac Allister flash a fourth-minute volley wide of the post in the first big chance for either team.
The Reds continued to come forward in droves, and the duo of Gakpo and Andrew Robertson were both thwarted by Guglielmo Vicario's double save in the 13th minute, exactly 13 minutes before VAR controversy reared its ugly head.
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During a 50-50 challenge, Jones's foot rolled over the ball and into the ankle of Yves Bissouma, which was originally deemed worthy of a yellow card by Simon Hooper, but he upgraded the Englishman's punishment after checking the monitor.
Tottenham almost took advantage of their extra man straight away, but Alisson Becker comfortably held onto James Maddison's 30th-minute curler, not long Luis Diaz finished across goal from Mohamed Salah's pass, but the offside flag saved Spurs' bacon.
That reprieve was just what the doctor ordered for Tottenham, who went down the other end and broke the deadlock with 36 minutes gone, as Maddison released Richarlison down the left with a sumptuous pass, and the Brazilian cut back for Son to tap home from close range.
Richarlison nearly went from assister to goalscorer in the 43rd minute, but his low effort struck the far post after an episode of pinball in the box, and the 10 men of Liverpool would claw their way back into the contest in the fourth minute of added time.
Dominik Szoboszlai was unsurprisingly at the heart of the move, crossing to Virgil van Dijk at the back post, and the Dutchman headed down for his compatriot Gakpo, who swivelled and fired home past Vicario.
However, Gakpo hurt himself in the process was replaced by Jota for the second half, in which Spurs exploded out of the blocks in a bid to restore their narrow lead.
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In a tale as old as time, Liverpool were indebted to Alisson, who produced an amazing fingertip save from Maddison in the 50th minute, only one moment before tipping Son's volley over the top to keep the Reds on level terms.
The Richarlison-Son cutback combination ended with the latter's shot trickling over the line in the 59th minute, but Richarlison had made his run far too early, and the offside flag went up straight away.
The 10 men of Liverpool were holding out valiantly, but their task became monumentally harder in the 70th minute, as Jota - who was already on a yellow card for chopping down Destiny Udogie - did so again from behind after losing the ball to the Tottenham left-back and followed Jones to the naughty step.
However, as much as Tottenham huffed and puffed, Postecoglou's men could not breach the Liverpool backline, but all of the Reds' valiant work was undone by a huge stroke of misfortune.
With their last attack down the right in the sixth minute of injury time, Porro sent in a low cross, and Matip stuck out a leg in an attempt to hack the ball away, but the Cameroonian defender diverted Porro's cross into the roof of his own net - leaving a stranded Alisson with no chance.
A mix-up between Van Dijk and Ryan Gravenberch saw Liverpool's final punt upfield fizzle out, as Spurs returned to second place in the table - above Arsenal on goals scored - while Liverpool sit fourth after losing in the top flight for the first time since April.
The Lilywhites now have a week to recover emotionally and physically before next weekend's trip to Luton Town, while the Reds return to Europa League action at home to Union SG on Thursday.
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