Tottenham Hotspur’s status as Premier League title chasers was seriously harmed on Saturday as they fell to a first defeat in seven league games.
The North London side gave away the lead to go down 3-1 at home to Wolverhampton Wanderers.
Harry Kane fired a largely unimpressive Spurs side in front midway through the first half, picking the ball up from deep out wide, cutting inside and finding the top corner from outside the area.
The goal was Kane’s fourth in three league games but was not enough to see off the dogged visitors.
Wolves had taken points off some of the biggest teams such as Manchester City, Arsenal, Chelsea and Manchester United in their return to the top flight.
Nuno Espirito Santo’s side levelled in the 72nd minute with a towering header from a corner from French defender Willy Boly.
Mexican forward Raul Jimenez then gave them the lead in the 83rd minute and Helder Costa sealed the win with a counter-attack goal in the 87th.
A first home defeat since late October leaves second-placed Tottenham six points adrift of Liverpool, who can widen that gap when they host Arsenal later on Saturday.
Manchester City could reclaim second spot if they win at Southampton on Sunday.