Manchester City had just secured their third Premier League title in a row and a fifth in the past six seasons.
A treble beckoned, with Manchester United and Internazionale ultimately taken down at Wembley and the Ataturk Olympic Stadium to seal a place in history for Pep Guardiola and his players.
In an interview with Sky Sports in late May 2023, Guardiola was asked what could be the next challenge after a treble-winning campaign.
“Score a goal against Spurs away,” he joked. “I stay because I want to beat Spurs away.”
The FA Cup fourth-round draw means Guardiola will get two bites at addressing one of the great peculiarities of English football before the end of 2023/24.
The Tottenham Hotspur Stadium opened in April 2019, with Spurs hosting City for the first time at their new home a week later. During a period when Guardiola’s men have been a dominant force, scoring goals by the bucketful and hoarding trophies, their record at this state-of-the-art north London venue has been absolutely abysmal.
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Over the course of five visits, City have lost five times to four different Spurs managers and failed to even score a goal, missing a couple of penalties along the way. On January 26, Guardiola gets another chance to scratch the itch, with Spurs under Ange Postecoglou a very different proposition to the versions put together by Jose Mourinho and Antonio Conte. Surely the record can’t hold?
Tottenham 1-0 Man City (Champions League: April 9, 2019)
Six days on from the inaugural game at the Tottenham Hotspur Stadium, Mauricio Pochettino’s Spurs welcomed their Premier League counterparts for the first leg of a Champions League quarterfinal. City actually had a golden opportunity to become the first visiting team to score at the new ground after 12 minutes, but Hugo Lloris guessed correctly and saved Sergio Aguero’s penalty.
A tense encounter unfolded and Guardiola kept Kevin De Bruyne and Leroy Sane on the bench until the 89th minute as he juggled the demands of battling for trophies on four fronts. Eleven minutes before that, Son Heung-min caught out Fabian Delph and fired a shot through Ederson to seal victory on the night. It would be the only game City lost in their final 23 matches of the campaign as they won a domestic treble but bowed out of the Champions League on away goals after a remarkable 4-3 victory over Spurs in the following week’s return clash.
Tottenham 2-0 Man City (Premier League: February 2, 2020)
Aguero won a first-half penalty, drawing a foul from Serge Aurier, but passed on responsibilities to Ilkay Gundogan following his mishap at the same end 10 months earlier. The result was the same, with Lloris diving to his left to repel the Germany midfielder’s attempt.
In what would become a common theme of these encounters, City proceeded to dominate possession and couldn’t find a way through. Oleksandr Zinchenko then brought down Harry Winks with an hour played to earn his second booking and Spurs led shortly afterwards through a fabulous volley from debutant Steven Bergwijn. Picking up another repeated narrative thread, Son thumped into the bottom corner to seal the points.
Tottenham 2-0 Man City (Premier League: November 21, 2020)
Mourinho made it back-to-back wins over his former Clasico rival, with Son on target once more to give Tottenham an early lead. City thought they had that elusive goal when Aymeric Laporte drilled beyond Lloris from a Gabriel Jesus knockdown, although replays showed the Brazilian handled to make the assist possible.
Giovani Lo Celso crowned a Harry Kane-orchestrated counter-attack to put Spurs top of the table after nine games, with City languishing in 12th having played one fewer. Guardiola’s side still managed to finish English football’s behind-closed-doors season as champions and beat Spurs a few days after Mourinho’s sacking in the Carabao Cup final, with Laporte the man on target in a 1-0 win.
Tottenham 1-0 Man City (Premier League: August 15, 2021)
It’s sometimes easy to forget Nuno Espirito Santo’s 17-game tenure at Spurs happened at all, but it started in fine fashion with a win over the Premier League champions. Guardiola handed a full debut to £100m man Jack Grealish, with a slightly mix-and-match feel to his line-up following their European Championship commitments.
Once again, City were left to rue missed chances after dominating possession. Once again, Son rattled a shot past Ederson. Rinse and repeat.
Tottenham 1-0 Man City (Premier League: February 5, 2023)
Antonio Conte’s most notable success against City came amid a Kane masterclass at the Etihad Stadium in February 2022, when the England captain responded to Riyad Mahrez’s injury-time equaliser from the penalty spot with an even later winner to seal a 3-2 triumph. Spurs were also 2-0 up in the corresponding fixture in 2022/23 before Mahrez inspired a rip-roaring 4-2 win for the hosts.
All of that counted for nothing as an off-colour City reverted to type in a match where there was a sense of peculiar inevitability after Kane opening the scoring in the 15th minute. Even Erling Haaland, on his way to a record-breaking Premier League season, could not break the spell. The only unusual thing was Son not finding the net before being substituted in the 84th minute. Cristian Romero was then sent off but Guardiola’s team ran out of time to capitalise.
Tottenham vs. Man City FA Cup history
If you want strange things to stop happening between Tottenham and Manchester City, the FA Cup might not be the ideal forum. The clubs have met eight times in England’s famed knockout competition, collecting three wins apiece.
Two of their most famous encounters came in the 1981 FA Cup final, which went to a replay after City midfielder Tommy Hutchison claimed the unusual distinction of scoring at both ends in the showpiece, having given John Bond’s side the lead with a flying header before diverting a Glenn Hoddle free-kick into his own net.
The return to Wembley five days later produced a classic encounter and one of the iconic FA Cup goals. A mazy 76th-minute dribble and finish through an exhausted opposition defence by Spurs hero Ricky Villa might not have even been the best goal of the game, considering teenager Steve Mackenzie’s exquisite volley to equalise for the City during the first half, but the drama and significance of the moment made it one of the most celebrated strikes ever under the old twin towers.
City had not reached a major cup final since when they hosted Tottenham at Maine Road in 1993. A capacity crowd were treated to an early opener from Mike Sheron before Spurs dismantled Peter Reid’s side. Nayim, a couple of years before infamously embarrassing David Seaman from near the halfway line, claimed a fine hat-trick from more conventional range.
At 4-1 down, home full-back Terry Phelan embarked upon a surging run for an incredible solo goal. This prompted a spew of various emotions from the disgruntled home supporters, a few hundred of whom invaded the pitch, variously to protest against unpopular chairman Peter Swales and taunt the celebratory Spurs fans packed into the North Stand.
The teams left the field and police horses were required to bring a semblance of order. When the game resumed, Spurs won a penalty. Teddy Sheringham blazed it wide. Given the tinderbox atmosphere, it was probably for the best.
Considering all that went on, it’s perhaps surprising that game doesn’t have its own Wikipedia page. The 2004 fourth-round replay between Spurs and City at White Hart Lane does, having produced one of the most astonishing turnarounds in the century-and-a-half history of the competition.
Following a 1-1 draw in Manchester, Tottenham ran amok before halftime and Christian Ziege’s free-kick shortly before the interval had them 3-0 up and cruising into a fifth-round trip to Manchester United. City had already lost star striker Nicolas Anelka to injury and, foreshadowing the social media landscape 20 years hence, Joey Barton couldn’t stop saying stupid things and was sent off for dissent.
Three goals and a man down, City’s goal early in the second period through captain Sylvain Distin felt inconsequential. It was only when Paul Bosvelt’s deflected effort spun into the net with 20 minutes still to play that things threatened to get interesting or, if you like, implausibly Spursy.
Shaun Wright-Phillips found an majestic dinked finish to level the game, by which point the hosts’ composure had entirely deserted them. In the final minute, Michael Tarnat swung a cross to the far post and Jon Macken headed past Kasey Keller.
If a City team operating in such complete shambles can score four times in a half at Tottenham, you’d think Guardiola’s celebrated vintage might finally muster at least one on Friday.
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