The Centurions, treble winners, four consecutive Premier League titles and plenty more in between. There’s nothing that Manchester City haven’t done in the current era of English football. Yet, amid all of that historic success, they just haven’t been able to guarantee a way past several Tottenham Hotspur sides.
It’s one of the Premier League’s greatest mysteries and one that will likely remain unsolved,so much so that Pep Guardiola’s side must be dreading every meeting with the Lilywhites.
With that said, we’ve taken a look back on 10 times that Spurs shocked Manchester City.
1 Man City 0-1 Tottenham, May 2010 Crouch snatches CL football for visitors
Before Manchester City found themselves dominating under Pep Guardiola, they were at the very start of their project in 2008 and seeking Champions League qualification. In a sign of things to come, however, it was Spurs and Harry Redknapp who denied Roberto Mancini’s side, much to the shock of the rich new owners of the Citizens.
Hero of the hour Peter Crouch bundled home in dramatic fashion to see the north London side leap ahead of their opponents in pursuit of a place among Europe’s elite, as Spurs proved that money didn’t equal instant success in the Premier League.
2 Tottenham 3-1 Man City, April 2013 Spurs dent City's title hopes
Just three years later, City were firmly in the title picture and their project was flying under Mancini. Yet, the same constant remained. When it mattered most, they still couldn’t find a way past Spurs, who this time came from behind to shock the champions.
Of course, that comeback victory proved to be all-important, too, given that it was Manchester United who picked up the Premier League title that year in Sir Alex Ferguson’s final season.
Samir Nasri initially got his side off to the perfect start before Spurs hit back through Clint Dempsey and Jermain Defoe to turn the game on its head. Adding the gloss on an impressive victory, Gareth Bale returned from injury with a bang by audaciously dinking a third past a beaten City side.
3 Tottenham 4-1 Man City, September 2015 Pochettino's men sweep City aside
A year before the arrival of Pep Guardiola, it was Manuel Pellegrini in charge at Manchester City, who also fell victim to Spurs during his tenure. This time, the Lilywhites didn’t just edge past the Manchester side, either – they sent them packing in style.
Kevin De Bruyne ensured that the Citizens were off to a good start once again, but it was to no avail. Eric Dier struck just moments before half-time and the momentum shifted from there.
Just five minutes after the break, it was the turn of Toby Alderweireld to take the advantage for his side before Harry Kane and Erik Lamela left their own marks on the Citizens.
It was a sign of things to come for Spurs that season, who challenged shock champions Leicester City in their most impressive campaign under Mauricio Pochettino.
4 Man City 1-2 Tottenham, February 2016 Spurs complete shock double
In the middle of a title charge against Leicester, a trip to the Etihad was the ultimate test for Pochettino’s side. They passed with flying colours as Christian Eriksen’s late winner ensured that they completed a shock double over Manchester City.
This time, it was Spurs who opened the scoring through Harry Kane’s penalty in the 53rd minute, before Kelechi Iheanacho levelled things up with just 16 minutes remaining.
Just when the Lilywhites may have been left to settle for a point, Eriksen struck to seal the three points in the 83rd minute. Spurs had once again shocked Pellegrini and City.
5 Tottenham 2-0 Man City, October 2016 Spurs deal Guardiola first defeat
When Pep Guardiola arrived, many may have believed that would be the end of Tottenham’s joy over Manchester City, but they couldn’t have been more wrong. In fact, it’s quite fitting that it was the Lilywhites who handed the Spaniard his first defeat in charge of the Manchester club.
Once again, White Hart Lane was a fortress. Guardiola and his side arrived on a run of six straight victories and ready to end any misfortune that they had been facing in north London. Spurs, meanwhile, were simply ready to cause another shock and welcome Guardiola to the Premier League once and for all.
Defeating Guardiola’s side 2-0, Spurs got off to the perfect start when Aleksandar Kolarov’s own goal opened the scoring inside 10 minutes, before Dele Alli put his side in a commanding lead to seal all three points before half-time.
6 Man City 4-3 Tottenham, April 2019 Spurs survive to send City packing in Champions League quarters
Back when away goals were a thing, the Champions League was full of some historic drama, and Guardiola’s Manchester City side felt the full impact of that in 2019.
It simply had to be Spurs who stood in their way as Manchester City went in pursuit of their first-ever Champions League trophy.
Perhaps the cruellest game on this list, Son Heung-min’s brace and goals from Raheem Sterling and Bernardo Silva – including four goals in the first 11 minutes – left the game level at 3-3 before the referee could even blow for half-time.
The greatest drama came after the break when Fernando Llorente’s controversial 73rd-minute goal handed Spurs the advantage on away goals to cancel out Sergio Aguero’s earlier strike. Set up for one last moment of madness, Raheem Sterling thought he’d won it at the death before VAR intervened to leave Guardiola on his hands and knees in pure disbelief – and Spurs through to the last four.
7 Tottenham 2-0 Man City, February 2020 Mourinho shocks Guardiola's champions
In a season that saw Guardiola’s side fall apart and Liverpool dominate on their way to their first-ever Premier League title before the pandemic stole the headlines, Jose Mourinho got one over on his old foe.
It turned out to be one of Mourinho’s most memorable games in charge and one of Steven Bergwijn’s best games in a Spurs shirt, albeit his first. The debutant came from the bench to help his side complete the smash-and-grab win after Oleksandr Zinchenko was given his marching orders.
Superbly volleying home to announce himself just after the hour mark, Bergwijn’s debut delight was followed by Son’s effort to seal another victory over Guardiola.
8 Tottenham 1-0 Man City, August 2021 New manager, same Spurs
Perhaps selling many a dream, Nuno Espirito Santo became the latest manager to defeat Manchester City in what was beginning to feel like a north London tradition. On his debut of all games, the former Wolverhampton Wanderers boss overcame Guardiola’s side without an exit-linked Harry Kane in controversial fashion courtesy of Son’s statement-making strike.
Of course, Espirito Santo didn’t start as he meant to go on, as his spell in charge ended in a case of what might have been rather than one full of the expected success after a debut to remember.
9 Man City 2-3 Tottenham, February 2022 Kane seals late, late show
Just when Riyad Mahrez believed that he’d rescued a vital stoppage-time point, Spurs left Guardiola in shock once again. The Lilywhites looked down, out and ready to settle for a point. But Kane wasn’t. The star striker led by example to find a dramatic winner in what was virtually the last kick of the game just three minutes after Mahrez’s equaliser.
It remains one of the most dramatic moments on this list. Even as Manchester City still went on to win the Premier League title that year, Spurs had another moment to remember against the Citizens.
10 Tottenham 2-1 Man City, October 2024 Spurs begin City's losing run
Fast-forwarding to the latest moment to savour for Spurs against Manchester City, the Lilywhites kickstarted the champions’ four-game losing run in all competitions by sending them packing in the Carabao Cup.
History suggests that goals from Timo Werner and Pape Matar Sarr won’t be the only goals that Ange Postecoglou’s side manage against those at the Etihad this season. Even after suffering defeats against Crystal Palace and Ipswich Town in their last five games, defeating Manchester City twice would be fairly fitting in what can and will forever be the history of Tottenham Hotspur.