Ten-man Manchester City gave up a two-goal lead as they crashed to a 3-2 defeat by Wolverhampton Wanderers at Molineux on Friday to leave them 14 points adrift of Premier League leaders Liverpool.
The 89th-minute winner from Matt Doherty means Liverpool have a 13 point lead over second-placed Leicester City, who they beat 4-0 on Thursday, and Juergen Klopp's side have played one game less than their two challengers.
"Nobody expected us to be this far away from Liverpool at this halfway point," said City midfielder Bernardo Silva.
"We have to continue now. We know that winning the title is very complicated. I wouldn't say impossible but very difficult."
Wolves, who also beat City 2-0 in October, became just the second team to complete a league double over Pep Guardiola's side, following Chelsea in 2016-17 and it was another comeback triumph for Nuno Espirito Santo's team.
The Midlands side have now won 14 points from losing positions this season, more than any other team in the league.
City's Brazilian keeper Ederson was sent off in the 12th minute after he raced out of his area and clipped Diogo Jota, who tumbled to the floor.
The VAR review backed referee Martin Atkinson's decision but the system was soon back to familiar controversy when it awarded City a penalty — ruling that Leander Dendoncker had trod on the foot of City winger Riyad Mahrez.
Wolves keeper Rui Patricio saved Raheem Sterling's spot-kick, but VAR spotted an encroachment in the area by Conor Coady who had cleared the loose ball and so the penalty had to be retaken. Again, Patricio saved from Sterling but this time the England winger drove home the rebound to put City in front.
Sterling then doubled City's lead, five minutes after the interval, with a composed finish after had been sent clear by a defence-splitting pass from Kevin De Bruyne.
Wolves got back into the game though, five minutes later, when Adama Traore, who had scored twice in Wolves' win at City in October, beat substitute keeper Claudio Bravo with a low drive from outside the area.
It was poor defending from City full-back Benjamin Mendy that handed Wolves the equaliser with less than ten minutes remaining. The Frenchman trying to usher the ball out for a goal kick was robbed by Traore, who zipped a low pass across the goal to Raul Jimenez, who slotted home.
The dramatic winner came in the 89th minute when Matt Doherty weaved his way through the City defence before poking a left-foot shot past Bravo.
There was still time for Sterling to hit the bar with a stoppage-time free-kick but it was not to be for the defending champions.
"Eighty minutes 10 against 11 is so tough, so demanding. We could not defend the result," said Guardiola.
"We have to think of the next game and about winning our games. It's unrealistic to think about (catching Liverpool). In 48 hours we have another game," added the Spaniard.
Espirito Santo said his team had delivered a memorable evening for their supporters.
"It was a good night, a very good night. The game was fantastic. Everything changes with City with one man less but it was very good," he said.