ANGE POSTECOGLOU fell to his knees in despair after Pedro Porro failed to convert a golden opportunity against Liverpool.
Tottenham secured a shock 1-0 victory over Arne Slot's side after enjoying the better chances in the Carabao Cup semi-final first leg.
Spurs worked hard but frustrated the home fans after missing several chances to take the lead against Liverpool.
But Postecoglou couldn't believe his eyes when Porro missed two glorious chances in a row from close range in the 55th minute.
Alisson was caught napping on the ball by Lucas Bergvall, who brilliantly chased the Brazilian into his area.
The hard-working 18-year-old then reappeared behind the sloppy Alisson to poke the ball into Porro's path.
Porro's first shot was blocked by Virgil van Dijk before the ball quickly bounced to Bergvall, who put Porro through again.
But the Spanish full-back failed to convert from eight yards as he went wide with the goal gaping.
A perplexed Postecoglou turned to his bench in disbelief before falling to his knees in pain.
It's been a slow start to 2025 for Liverpool, who dropped points against Man Utd on Sunday and were below their best tonight.
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Meanwhile, Spurs midfielder Rodrigo Bentancur was rushed to hospital after suffering a sickening fall within 15 minutes.
The midfielder landed awkwardly after trying to head the ball unchallenged from a corner.
Former Anfield striker Dominic Solanke had a brilliant finish in the 77th minute but was disallowed after being ruled marginally offside.
But Bergvall stole the show when his first club goal put Spurs 1-0 ahead with four minutes of normal time remaining.
Liverpool manager Slot was furious as Bergvall had seemingly escaped a second yellow card just a minute before scoring.
The Swedish midfielder was shown a yellow card before charging into Liverpool full-back Kostas Tsimikas.
Injury rules meant Tsimikas had to leave the field and wait ten seconds as Spurs scored their winner.
Meanwhile, Liverpool's 24-match unbeaten run came to an end, hosting Spurs in the second leg on February 6.
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