Defending champions Manchester City remain 22 points behind Premier League leaders Liverpool.
Pep Guardiola's men missed a penalty and had a player sent off in a 2-0 defeat to Tottenham.
Both the goals came after City defender Oleksandr Zinchenko was sent off in the 60th minute for a second bookable offence.
Newly signed Dutch winger Steven Bergwijn (63') scored on his debut, while Son Heung-min doubled the lead just eight minutes later.
Spurs have moved up to fifth in the table, four points behind fourth-placed Chelsea.
Elsewhere, Arsenal have now drawn their last four top-flight games after their match with Burnley finished goalless.


Ailing Sinner knocked out in French Open second round by Cerundolo
French teen Kouame reaches French Open third round in five-set thriller
Neymar out of Brazil friendlies and set to miss World Cup opener
Gucci to take over title sponsorship for F1's Alpine in 2027
Mateta fires Crystal Palace to Conference League crown
