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Man City 4 - 3 Tottenham - 17 April 2019
The iconic Champions League match between the two sides in April 2019 was played outside the Premier League's jurisdiction, but the drama it provided was too great to ignore.
Tottenham had beaten City 1-0 in the first-ever game at the Tottenham Hotspur stadium, meaning that Spurs entered City’s fortress with a small advantage.
Most were expecting a cagey, defensive encounter where Pochettino’s men sat back and weathered the storm, but those ideas were quickly put to bed after 3 goals were scored in 10 minutes.
Raheem Sterling struck after just four minutes, before Son Heung-Min achieved a brace just six minutes later. Bernardo Silva levelled the scores immediately after and Sterling added another goal in the 21st minute.
Sergio Aguero netted shortly after half-time to give City the advantage, however a controversial Fernando Llorente strike put Spurs ahead again on away-goals.
As if that wasn’t chaotic enough, Sterling had a goal ruled out by the newly-introduced VAR in injury-time. Tottenham booked their first ever Champions League semi-final, whilst a cardigan-wearing Pep Guardiola held his head between his hands.
There would be even more drama to come as Tottenham miraculously reached the 2019 Champions League final with a stunning 3-2 comeback win over Erik Ten Hag’s Ajax.
Tottenham 3 - 2 Man City - 19 Feb 2022
The appointment of Antonio Conte had given Spurs fans the license to dream again, and perhaps the greatest moment of his reign so far occurred at the Etihad Stadium.
A late Harry Kane winner concluded a thrilling game where new signings Cristian Romero and Dejan Kulusevski impressed. Riyad Mahrez thought he had rescued a point just three minutes earlier before Kane, who City spent the summer courting, found himself once again in the headlines.
Tottenham completed the double over Manchester City in the 2021/22 season, as they had won 1-0 in the opening game - one of the few highlights of Nuno Esperito Santo’s short stint as Spurs boss.
Man City 4 - 2 Tottenham - 19 Jan 2023
Tottenham were in rotten form heading into 2023, but all seemed to be forgiven when they took a 2-0 lead at the Etihad Stadium.
Goals from Kulusevski and Emerson Royal put Spurs in pole position against their old foes, ironically to the delight of league-leaders Arsenal. The Gunners were briefly 8 points clear of the champions and had recently endured a fiery battle of their own against 3rd-placed Newcastle.
A Riyad Mahrez masterclass was to come, though, with the Algerian bagging two goals and creating another. World Cup winner Julian Alvarez bundled home, before an inevitable Erling Haaland goal leveled the scores.
Mahrez’s brace followed soon after, giving City a much-needed victory over Spurs and reigniting the title race once again.
The upcoming Spurs/City game has a hard act to follow given the quality of the previous meetings, and the inclusion of Arsenal in the title race has given this storied rivalry yet more depth.
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