Manchester City's 100% Premier League record came to an end at Molineux as Hwang Hee-chan scored a second-half winner to give Wolves a shock victory against the champions.
City manager Pep Guardiola, forced to watch from the stands as he served a one-match touchline ban, was unable to intervene as his side failed to take control in their usual manner and free-scoring striker Erling Haaland was limited to a single chance.
Still, it did seem as though the visitors were on course to emerge victorious after Julian Alvarez curled home a brilliant free-kick to level Ruben Dias' early own goal.
But, just as Pedro Neto had gone on a right-wing raid before the opener, Nelson Semedo's forward surge inspired a second for Wolves, who ended a run of six straight defeats against City.
It completed a miserable day for former Wolves midfielder Matheus Nunes.
The Portugal international went on strike to secure his £53m move to City last month and the home fans evidently have not forgotten as they jeered him every time he touched the ball before he was substituted at half-time.
Whilst most observers feel it is a foregone conclusion that City will become the first side in English football history to win four league titles in a row, there are signs to provide reason for optimism amongst their rivals.
City have now gone behind four times in their last five matches and have now lost successive games for the first time since January following their midweek defeat to Newcastle in the EFL Cup.
Although he was in an unaccustomed position alongside football director Txiki Begiristain, there was the familiar sight of Guardiola rubbing his head in frustration at a team that is struggling to find the fluidity they have been so accustomed to producing so easily.
Phil Foden tried his best to spark the visitors into life and Jack Grealish was introduced for the final 10 minutes to try to inspire a late revival.
It was not to be though, with Nunes' performance a clear disappointment as he struggled to impose himself on the contest and failed to reappear for the second half as youngster Oscar Bobb took his place.
There was an acceptance last season from virtually everyone at Wolves that at some point in the not too distant future, Nunes would leave.
But having haemorrhaged talent throughout a tortuous summer, it left a sour taste when the 25-year-old to refused to turn up and train in order to force his transfer to City.
When City's half-time change was announced to the crowd, the home fans reacted with glee, chanting "what a waste of money". When the final whistle sounded, the chant had changed to "Nunes, Nunes, what's the score".
Source: BBC