Tottenham Hotspur's alarming winter plight continued as West Ham United came from a goal behind to defeat Ange Postecoglou's men 2-1 at the Tottenham Hotspur Stadium.
Spurs exploded out of the blocks against their London rivals and deservedly went ahead through Cristian Romero, only to succumb to two unorthodox goals from Jarrod Bowen and James Ward-Prowse as their winless Premier League run stretched to five matches, while David Moyes's side have now avoided defeat in each of their last six across all tournaments.
Boasting just a single point from their last five Premier League contests, Tottenham have scored first in all of those encounters only to let victory slip from their grasp, becoming the first team in Premier League history to suffer such a fate.
Having sat on the naughty step for three games, Romero made a welcome return to the Tottenham backline, while ex-Arsenal goalkeeper Lukasz Fabianski made his first Premier League start of the campaign in place of the absent Alphonse Areola.
The former celebrated a dream comeback at Fabianski's expense with just 11 minutes gone, though, as Pedro Porro's outswinging corner was on the money for Romero, whose looping header nestled into the far side of the net for his third goal of the campaign.
Fabianski appeared bewildered by Romero's header - making no attempt to dive - but an early goal was no less than a fired-up Tottenham deserved, as Moyes's troops seldom enjoyed possession of the ball.
However, one such sequence just two minutes after Romero's opener saw Mohammed Kudus squander a gilt-edged opening, meeting Vladimir Coufal's ball to the near post but flashing his shot agonisingly wide.
Ange Postecoglou's side remained firmly in the ascendancy, though, and Fabianski had to get his gloves dirty to deny Giovani Lo Celso his third goal from as many games in the 35th minute, as the Argentine sent a venomous volley towards the Hammers goalkeeper.
Another golden opening for West Ham in the 44th minute also went begging, as Lucas Paqueta sent a free header into the ground and wide of the mark following excellent work from Kudus, before Kurt Zouma stuck a leg out to deflect a Lo Celso cross onto the upright in a final first-half scare for the visitors.
An early second-half fright also came the Irons' way, as Spurs appealed for a penalty when the ball struck Coufal's elbow in the 50th minute, but the Czech defender was moving his arm into his body at the time, so the hosts' pleas fell on deaf ears.
Only two minutes after that reprieve, West Ham benefitted from a highly fortunate double deflection to level matters against the run of play, as a Kudus strike ricocheted off of Romero and Ben Davies into the path of Bowen, who gratefully fired in his 50th Irons goal into the roof of the net.
Shell-shocked by Bowen's response, Tottenham were a shadow of their first-half selves, but the Lilywhites should have restored their lead in the 70th minute, only for an unmarked Richarlison to head Porro's cross millimetres wide of the post; the Brazilian would not be spared the shame of that miss, as West Ham bagged their second in even more bizarre circumstances in the 74th minute.
Destiny Udogie sold Guglielmo Vicario short from a backpass, and the Italian goalkeeper could only push the ball to the feet of Ward-Prowse under pressure from Bowen; the ex-Southampton man hit the post with his first strike before following up with a simple tap-in from the rebound.
An increasingly desperate Tottenham continued to be repelled by Moyes's well-drilled backline, and appeals for a second penalty - this time for a perceived Zouma handball - were also waved away in the final few seconds, as Moyes celebrated his first-ever Premier League win away to a Big Six side in 40 attempts.
While Tottenham remain fifth in the rankings despite a fourth loss from five games, the Lilywhites are now nine points adrift of leaders Arsenal, while ninth-placed West Ham have closed the gap to Brighton & Hove Albion to just one point.
An appetising home tie with Newcastle United is next up for Postecoglou's men on Sunday afternoon, a couple of hours after the Hammers travel to Craven Cottage to meet Fulham in another London derby.
