Pep Guardiola has done it all in the last eight years at Manchester City – be it breaking records or setting unprecedented standards in the Premier League – but that doesn’t mean he’s been without matches to forget in big games, from Tottenham Hotspur all the way to the Manchester derby.
Even as the momentum has swung entirely the way of the Citizens, Manchester United have managed to cause what now feel like upsets under various different managers attempting to replace Sir Alex Ferguson years after his departure.
A battered, beaten and down-trodden Manchester United have managed to throw things back to the good old days when Guardiola’s Manchester City side stood in front of them, and we’ve ranked the most shocking results over the last eight years ahead of Ruben Amorim’s first attempt to defeat the Spaniard as Red Devils boss this weekend.
7 Man Utd 1-0 Man City – League Cup 2016/17 Guardiola's first-season frustration
To prove that even the best need time to adjust to life in the Premier League, Guardiola struggled in his debut campaign at the Etihad compared to his incredibly high standards at least. Taking the then-champions to a third-place finish and 15 points adrift of eventual winners Chelsea, Guardiola saw his side humiliated against Everton at Goodison Park and felt his first taste of defeat in the Manchester derby, losing 1-0 in the League Cup.
In the Jose Mourinho vs Guardiola rivalry, it was the former who welcomed the Spaniard to his stomping ground of English football – a place he had long before made his mark. Squaring off in the round of 16 of the League Cup, it was Juan Mata’s goal in the 54th minute which proved to be the winner for the Red Devils to shock Manchester City.
6 Man City 1-2 Man Utd – Premier League 2019/20 Solskjaer crushes City's title hopes
One of Guardiola’s most frustrating seasons undoubtedly came in 2019/20, and Manchester United only compiled that misery. With Jurgen Klopp’s Liverpool in the middle of one of the most dominant starts in Premier League history, dropping just two points in the first half of the campaign, City were struggling with the injury to Ruben Dias and paid the ultimate price as a result.
Manchester United weren’t exactly in an excellent position themselves, however, having eventually finished 33 points adrift of champions Liverpool to set up quite the battle up against the Citizens at the beginning of a torrid festive period.
The Red Devils raced into control from the off and didn’t look back, with Marcus Rashford’s penalty in the 23rd minute quickly followed by Anthony Martial’s effort just six minutes later to hand his side a 2-0 lead. Nicolas Otamendi’s goal to halve the deficit with seven minutes remaining threatened a comeback only to be nothing more than a consolation for a defeated Manchester City side.
5 Man Utd 2-1 Man City – Premier League 2022/23 United revel in late turnaround
It was almost like the United of old when they turned the game on its head to defeat Manchester City 2-1 in the 2022/23 campaign. In a season that eventually saw the Citizens lift yet another Premier League title under Guardiola, they once again failed to come unscathed against their local rivals. At the time, it looked to be a major moment in the title race too, as United moved within a point of City and then-leaders Arsenal remained five points clear.
The eventual champions thought they were on course for all three points when Jack Grealish converted Kevin de Bruyne’s cross on the hour mark, before four minutes to forget turned the game on its head. First came the controversial strike of Bruno Fernandes as City were left waiting for an offside flag which never came. Then, to send the Old Trafford faithful into raptures, Rashford slammed home Alejandro Garnacho’s cross to score the winning goal in the 82nd minute.
4 Man City 0-2 Man Utd – Premier League 2020/21 United end Guardiola's Covid winning run
As United shocked Guardiola once again, it was probably a good thing that fans were still not allowed in attendance across the Premier League amid the Covid-19 pandemic. With or without fans, however, the Etihad would have been silenced when Fernandes opened the scoring from the spot within just two minutes to instantly hand City a mountain to climb.
The second half didn’t start much better for the Citizens either. Having come out from the break ready to turn things around and extend their 15-game winning run, City were once again left shell-shocked. This time, it was unlikely goalscorer Luke Shaw at the centre of the scenes, wheeling away in celebration just five minutes into the second period to send United on their way to victory.
3 Man Utd 2-0 Man City – Premier League 2019/20 Red Devils complete first double since 2010
As if Manchester City’s December defeat wasn’t bad enough, they were on the wrong end of the Manchester derby for a second time in the 2019/20 campaign when they visited Old Trafford. The Red Devils took full advantage of a season to forget for the Citizens, completing their first league double over their rivals since the 2009/10 campaign.
For all of Ole Gunner Solskjaer’s downfalls, not many can argue that he had Guardiola’s number both in the 2019/20 campaign and in other moments to remember. Once again, Martial found himself on the scoresheet against the Citizens, scoring the opening goal on the half-hour mark courtesy of Bruno Fernandes’ assist.
The scenes that Old Trafford will remember most, however, is the aftermath of Scott McTominay’s goal to seal the three points and send United fans into delirium. The Scot was perfectly placed to receive Ederson’s poor clearance and sensationally lob the helpless Brazilian from range to secure victory and a league double over Guardiola in style.
2 Man City 2-3 Man Utd – Premier League 2017/18 Pogba stars in sensational comeback
Football’s a funny game, isn’t it? In the same year that Manchester City wrote their name forever into the history books as the Premier League’s first centurions, they still could not find a way to complete a double over rivals Manchester United. Even after taking a 2-0 lead and cruising courtesy of goals within five minutes from Vincent Kompany and Ilkay Gundogan, Guardiola was left scratching his head on the losing side come full-time.
Simply put though, it was the Paul Pogba show at the Etihad. The Frenchman dragged the Red Devils back into the game, volleying Ander Herrera’s chested pass into the back of the net to sweep home an excellent move in the 53rd minute. But he didn’t stop there. With the Red Devils’ tails up, Pogba found a second to equalise just moments later.
This time heading home on the end of Alexis Sanchez’s pinpoint cross in behind City’s backline, Pogba left the Etihad crowd shellshocked. Once again, however, United were not done there. Flipping the game on its head entirely, an unmarked Chris Smalling side-footed his effort beyond Ederson on the end of Sanchez’s set piece to seal a stunning comeback in the 69th minute. City became unstoppable centurions, but could not find a way past their rivals on that day.
1 Man City 1-2 Man Utd – FA Cup 2023/24 Carrington graduates spark FA Cup victory
In what has been a trend over the years, Manchester City squared off against rivals Manchester United as Premier League champions last season and in the FA Cup final, of all games. Many expected the Citizens to sweep past Erik ten Hag’s United side who had just endured the ultimate season to forget. With the Dutchman’s job still in question too, Wembley defeat would have likely ended his tenure.
As ever though, Guardiola was left shocked as City’s rivals denied his side a league and cup double to win another trophy under Ten Hag – a fact he was often quick to remind reporters of as the pressure mounted a few months ago.
It’s not Ten Hag who deserves all of the credit, however, for this was a game centred around United’s academy graduates, who stole the show to seal the silverware at Wembley. In nine minutes to savour, Garnacho first struck on the half-hour mark, before fellow graduate Kobbie Mainoo stole the show with a second.
Jeremy Doku’s late consolation caused some nerves, but champions City could not complete their comeback and were once again – and perhaps more so than ever – left shocked by an out-of-form Manchester United side.