Tottenham saw their hopes of a top-four finish dealt a blow as Wolves produced a fantastic away performance to leapfrog the hosts in the Premier League with a 2-0 win.
Goals from Raul Jimenez and Leander Dendoncker gave the visitors a deserved lead at the break, with Antonio Conte's men producing a dire performance and failing to test Jose Sa adequately in the opening period.
Although they managed a better second-half performance, Spurs were unable to find a way past a Wolves backline with a better defensive record than all bar Manchester City in this Premier League season.
Out-of-form Spurs have now lost three consecutive league games, and the last time a Conte-managed team did likewise was Atalanta in November 2009.
Wolves, looking to bounce back from a midweek loss to Arsenal, required just five minutes to take the lead. Hugo Lloris got down to stop Ruben Neves' strike before inexplicably flapping at Dendoncker's tame rebound, allowing Jimenez to volley home.
The France goalkeeper was again at fault when the visitors doubled their lead on 17 minutes, with his terrible pass inviting Wolves to press high, and Dendoncker tapped in his first goal of the campaign after initially hitting the post.
A furious Conte changed system when bringing on Dejan Kulusevski before the half-hour mark, but tame efforts from Harry Kane and Son Heung-min were the sum of Spurs' poor first-half efforts.
The visitors almost started the second half in the same manner as the first, when Jimenez forced a crucial save from Lloris at his near post, before Kane finally tested Sa twice before the hour mark.
Harry Winks' deflected volley clipped the post as the hosts tried to up the ante, before Kulusevski went close with a well-struck effort.
Wolves were content to sit deep and held on for what could be a crucial result in their own charge for European football, Sa making a fine late stop from Cristian Romero's header.
What does it mean? Wolves leapfrog Spurs by continuing away run
Wolves' victory, their third in their past four Premier League trips to Tottenham, took them a point above their hosts in the Premier League table after playing a game more, damaging the Champions League hopes of Conte's men and boosting their own chances of qualifying for European football.
Wolves have now won four successive top-flight away matches for the first time since April 1980, when they managed a run of five under John Barnwell's management.
Jimenez strikes early blow on fertile ground
Coming after five minutes and 58 seconds, Jimenez's opener was Wolves' fastest goal of the Premier League season to date.
The Mexican striker has now hit four goals in six Premier League appearances against Tottenham, and also netted in away wins over them in December 2019 and March 2020.
Spurs fail to respond
Spurs' terrible start to the contest left then 2-0 down at half-time of a Premier League game for the first time since December 2019, and they've still never come back to win from such a deficit on the own turf in the competition's history, managing four draws and 19 losses from such positions.
What's next?
Conte's Spurs will now prepare for a tough trip to the Etihad Stadium to face champions Manchester City next Saturday. Wolves, meanwhile, host Leicester City at Molineux this time next week.