Luis Diaz rescued a point for Liverpool but their title ambitions were rocked with a 1-1 draw against Tottenham on Saturday evening.
Son Heung-min fired Spurs into the lead in the 56th minute following a lively but goalless first half before Diaz drew the Reds level with a strike from range which took a wicked deflection off Rodrigo Bentancur to leave Hugo Lloris stranded. Liverpool dominated possession and had the lion's share of the chances but struggled to break down their stubborn visitors, who defended in numbers and with vigour.
The result could prove to be a hugely damaging one as Jurgen Klopp's side bid to win the title, as it leaves them top of the Premier League table only on goal difference and they will find themselves three points behind Manchester City if they defeat Newcastle on Sunday. Tottenham, meanwhile, picked up a valuable point in their bid to finish in the top four.
Here are five talking points from Anfield.
Spurs double-up
How do you stop the likes of Mohamed Salah, Sadio Mane and Luis Diaz? Tottenham's solution was to surround the Liverpool trident with bodies whenever they received the ball, attempting to suffocate them and deny them the space they need to flourish.
This strategy was effective even if it did leave gaps between the lines, although Jurgen Klopp will have been frustrated at how his side did not exploit these spaces. The Reds perhaps missed the presence of Naby Keita in midfield, as the Guinean likes to drive with the ball at his feet.
Jordan Henderson, who started the match as one of the hosts' No. 8s, is more inclined to offloading the ball than dribbling. That being said, the captain's reading of the game and tackling were vital at times and he made a number of crucial interventions, chief among which was his well-timed challenge to deny Harry Kane in the 12th minute.
Alexander-Arnold's reminder
One of the criticisms frequently levelled against Trent Alexander-Arnold relates to his ability to defend one-on-one. His creative output is fabled - he has 12 Premier League assists to his name this season - but many fans suspect he is vulnerable when left exposed against world-class wingers.
Well, he certainly came up against an elite wide-man in Son Heung-min, who arrived at Anfield having just taken his tally to 19 league goals for the season with a double against Leicester. There were fears the South Korea international would have a field day against Liverpool's high defensive line, especially as Spurs would likely be looking to hit their hosts on the counter-attack.
However, Alexander-Arnold dealt with the threat Son posed with composure to remind onlookers he has far more in his locker than a wicked delivery. Admittedly, things grew more frantic at the back for Liverpool after Son opened the scoring after the Spurs No. 7 left his berth on the flank to float across the front line.
Can Liverpool still win the title despite drawing with Tottenham? Have your say in the comments...
First-half finale
Although neither side could open the scoring in the first 45 minutes, it was an entertaining affair and the match came to life in the final moments before the interval. Hugo Lloris made a fine stop to deny Luis Diaz, there were Liverpool penalty appeals after Trent Alexander-Arnold went down in the box and, at the other end, Pierre-Emile Hojbjerg hit the post as Tottenham broke.
Virgil van Dijk also clipped the top of the bar from Andy Robertson's corner shortly before the flurry of activity and there was a sense a goal was coming for the hosts. As such, Spurs were likely the happier of the two teams as the half-time whistle was blown, giving them the respite they needed after 45 minutes of body-on-the-line defending during which they only had one-third of possession.
At times, Tottenham were better without the ball than with it as many of the chances they gave up came from trying to play out from the back against a typically-ruthless Liverpool press.
Son stuns hosts
The amassed Anfield faithful could only watch on as Liverpool's hopes of the quadruple seemed to vanish into thin air 11 minutes into the second half. Son Heung-min tapped in from Ryan Sessegnon's square pass to cap a fine Tottenham move which stunned the hosts and delivered what appeared to be a fatal blow to the Reds' title bid.
It was the 20th Premier League goal of the season for the 29-year-old, who is undoubtedly one of the biggest stars in the top flight and continues to post truly remarkable numbers in the Spurs attack.
Klopp and Diaz respond
Jurgen Klopp wasted little time after falling behind and sent on Kostas Tsimikas and Diogo Jota for Andy Robertson - who was partly at fault for Tottenham's goal - and Jordan Henderson respectively. This saw Liverpool shift to a front four, leaving Fabinho and Thiago as the two in midfield.
It took until the 74th minute for the hosts to hit back through Luis Diaz, who has quickly established himself as a fan favourite on Merseyside following his January arrival. The all-action Colombia international benefitted from a hefty deflection as his effort from just outside the area nestled in the bottom corner, prompting huge celebrations and a renewed roar from the home fans.
However, the equaliser came too late for Liverpool and they could not find another goal in the remaining 15-or-so minutes as Spurs continued to defend in numbers. The Reds will be particularly disappointed not to have made more of the glut of set pieces which came their way, as they did not pose their usual cutting edge from corners and free kicks.
