Luis Diaz spared Liverpool a rare Anfield defeat, but a 1-1 draw with Tottenham on Saturday represents a major blow to the Reds' title ambitions.
Son Heung-min left the famous old stadium shaken early in the second half when he tucked in from close range to give Antonio Conte's visitors a shock lead.
That was his 20th league goal of the season, and Liverpool knew anything other than a win would put City within sight of the Premier League trophy.
Liverpool have an unprecedented quadruple in their sights, and Diaz's deflected strike for an equaliser in the 74th minute just about kept the dream alive, but hopes might be fading. They go top for now, level on points with a City side who have a game in hand, against Newcastle United on Sunday.
Mohamed Salah and Harry Kane had early shots blocked, before Virgil van Dijk nodded wide after getting on the end of an outswinging Andy Robertson corner from the left.
A misdirected defensive header from Ryan Sessegnon almost gave Salah a tap-in, but Hugo Lloris was alert to the danger.
Van Dijk headed against the top of the Tottenham crossbar from a Trent Alexander-Arnold corner, before Luis Diaz drew a save from Lloris with a fizzing low strike. Pierre-Emile Hojbjerg served a reminder of the visitors' threat when his skidding drive hit the outside of the left post.
Liverpool were full of purpose, swarming and probing early in the second half for the big chance that might bring a breakthrough.
However, they were stunned by Son in the 56th minute, when he slotted past Alisson after Kane's pass to Ryan Sessegnon on the left was followed by a sharp centre to the unmarked South Korean.
Jurgen Klopp threw on Diogo Jota, looking for a spark, and Salah soon had a great chance as he cut inside on his left foot, only for Ben Davies to produce a glorious block.
Diaz hit the equaliser when his 22-yard strike took a massive deflection past Lloris, finding the bottom-left corner, and try as they did, Liverpool could not find a second.
What does it mean? Advantage City
They will have been celebrating this result in Manchester, even though it could have worked out even better for City.
Liverpool were looking to make up ground on City this weekend, but the likelihood is they will fall three points adrift, unless Newcastle cause a sensation at the Etihad Stadium. Liverpool are unbeaten in 22 Premier League home games now, but their 12-game winning streak in the competition at Anfield is over.
Super Son hits landmark for Spurs
Son's feat in reaching 20 Premier League goals this season is made all the more remarkable by the fact none of them have been penalties.
He becomes just the second Tottenham player to reach 20 in a Premier League campaign without any of them being spot-kicks, after Gareth Bale in 2012-13.
Klopp denied by Anfield draw specialist Conte
Spurs boss Conte knows what it takes to win championships, having done so with Juventus and Inter in Serie A, and with Chelsea in the Premier League. His team dealt Liverpool a colossal blow to hopes of finishing with the silverware, and the result perhaps should not have come as a surprise. Both of Conte’s previous Premier League visits to Liverpool finished in 1-1 draws, so this completes a hat-trick.
It also puts Conte in a group of five managers to have avoided defeat in each of their first three away games at Anfield in the competition, joining Martin O’Neill, Peter Reid, Roy Hodgson and Paul Lambert.
Key Opta Stats:
- Son has both scored (12) and been involved in (17) more Premier League goals than any other player in 2022.
- Salah made his 250th appearance for Liverpool. Despite failing to score in this game, he has still scored more goals (155) than any other Premier League player in all competitions since his debut in August 2017.
- Liverpool have only lost one of their last 28 Premier League home games against Tottenham (W18 D9), and are unbeaten in their last 11 since a 2-0 loss in May 2011 (W7 D4).
- Tottenham are the first side to stop Liverpool from winning at Anfield in the Premier League since Brighton in October 2021 (2-2).
- Spurs have lost just one of their last eight Premier League games (W5 D2), with that defeat coming at home to Brighton last month.
Liverpool are set for a reunion with former skipper Steven Gerrard when they head to Aston Villa on Tuesday. Tottenham have their own big midweek game when they tackle north London rivals Arsenal on Thursday.