Liverpool’s Premier League title hopes suffered a huge blow even though they went top of the table as Tottenham clung on for a 1-1 draw at Anfield on Saturday.
The Reds edged ahead of Manchester City on goal difference, but the English champions can now afford to draw one of their remaining four games and still retain their title.
Pep Guardiola’s men can retake top spot and open up a three-point lead when they host Newcastle on Sunday.
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A share of the spoils took Tottenham to within a point of fourth-placed Arsenal, but their chance of a top-four finish now also rely on the Gunners dropping points in two of their final four games.
Son Heung-min rounded off a brilliant team move to put Spurs in front on 56 minutes.
Luis Diaz’s deflected shot levelled 16 minutes from time, but Jurgen Klopp’s men failed to find a winner.
Twenty-one points separate the sides, but Spurs have made a habit of saving their best for the big occasion.
Antonio Conte’s men are unbeaten in all four meetings with City and Liverpool this season.
Liverpool did not start like a side fatigued by reaching the Champions League final in their 57th game of the season against Villarreal in midweek, as the intense press from the home side penned Tottenham in.
However, the visitors were first to seriously threaten when Alisson Becker had to be sharp off his line to prevent Harry Kane’s cross reaching Son and Rodrigo Bentancur fired the follow-up far too close to the Brazilian stopper.
Liverpool’s best efforts before the break came from set-pieces as Virgil van Dijk hit the crossbar, while Diaz also tested Hugo Lloris after being teed up by Sadio Mane.
Spurs also hit the woodwork in the first-half when Pierre-Emile Hojbjerg took aim from long range.
The second-half followed the same pattern, with Liverpool camped in the Tottenham half, but this time Spurs did pick them off on the counter-attack.
Kane was given time to assess his options and picked out Ryan Sessegnon who slid the ball across the box for Son to tap in his 20th Premier League goal of the season to move within two of Mohamed Salah.
It was the first time Liverpool have trailed at Anfield in a league match since February and Spurs could have doubled their lead had Son controlled another Sessegnon cross moments later.
Salah did his best to extend his advantage in the race for the Golden Boot and rescue the Reds’ title challenge only to be denied by a brilliant block from Ben Davies.
Diaz swung the match and the tie in midweek as Klopp’s men came from 2-0 down on the night to win 3-2 against Villarreal and reach a third Champions League final in five seasons.
The Colombian has been a sensational signing since arriving in January and made another contribution with a slice of fortune.
Diaz’s shot from outside the box took a huge deflection off Bentancur to wrong-foot Lloris.
But Liverpool will have to settle for a shot at cup glory unless City stumble as Tottenham held firm in the closing stages.
Klopp’s men, who have already lifted the League Cup, face Chelsea in the FA Cup final next weekend and then Real Madrid for the European Cup in Paris on May 28.