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Tottenham vs Manchester United: Memorable moments

Tottenham Hotspur has faced Manchester United 204 times since their first meeting in 1899. Here are some memorable moments between Tottenham and Manchester United in recent years.

Moinak Banerjee
Last updated: 19.05.2025
Tottenham vs Manchester United best matches

Tottenham Hotspur has faced Manchester United 204 times since their first meeting in 1899. Although United has a historical advantage with 96 wins, this fixture cannot be considered one-sided for either club, particularly in the modern era. Here are the detailed stats on Tottenham vs Manchester United Head to Head


The power dynamic might have rested with the record Premier League winners, but the opposition have also had a say in crucial stages. This game has been better known for the stunning comebacks made by the Red Devils during Alex Ferguson's era. Lately, the fixture has produced some sensational results, going in Spurs’ favour. The meeting has always been played with great enthusiasm and high spirit.                 


Here are some memorable moments between Tottenham and Manchester United in recent years: 


Man United 2-1 Spurs: 1998/99 Premier League Title Clincher (May 16, 1999)


Manchester United chased a historical treble in the 1998/99 season, but it was not a straight cut for the side. In the Premier League, the Red Devils under their legendary coach Alex Ferguson were not outright favourites for the title as both North London clubs, Chelsea and Arsenal, were giving them a stiff challenge. The Blues were in a good position to snatch the title although their slump in the penultimate month of the season and the Gunners screwing their opportunity in the second-last game to retain the title made everything to be decided on the final day. United needed a win to have any chance to secure their fifth Premier League title otherwise, Arsenal would be champions, making their final assignment of the campaign against Tottenham Hotspur a tad more difficult. The alarm bell rang when the Red Devils fell behind in the 24th minute, with Les Ferdinand silencing Old Trafford. With odds pinned against them, Ferguson’s side started what will be a string of comeback fights against Spurs that became a legacy of this fixture. United’s poster boy, David Beckham's ecstatic equaliser just before half-time, set the stage for Andy Cole's lobbed winner to spark wild celebrations, securing a fifth Premier League title and the first trophy of United’s memorable treble. 


Spurs 3-5 Man United: Second-half turnaround (September 29, 2001)


Two years later, another remarkable comeback story unfolded in this fixture, which also became one of the highest-scoring matches in Premier League history. Defending champions Manchester United made the trip to White Hart Lane, coming off a disappointing 2-0 defeat to Deportivo La Coruna in the Champions League, while the hosts were on a winless run at home since the start of the season. So, Glenn Hoddle’s team were desperate to change things around and stunned the visitors with their first-half performance. New signing Dean Richards gave the home side the lead inside 15 minutes, followed by Ferdinand scoring against the red shirts again from Poyet’s pass. As if the deficit were not enough, Christian Ziege, creator of the first goal, made it 3-0 with Poyet setting a goal again, putting Spurs into dreamland. Not many sides were capable of outplaying Ferguson’s United like that and scoring three in one half, forcing the guests to make a fitting response or face the heat. 


Few could have predicted what transpired in the second half as Ferguson again swung his wand of turnarounds. United came out as a transformed side, pulling one back instantly after the restart through Cole’s header from Beckham's cross. That goal created belief, causing United to upscale their attack, adding another around the hour mark when Laurent Blanc outjumped Ledley King to head home Beckham’s corner. Spurs, who were thumping their chests, now looked shaky, with their fear confirmed when Van Nistelrooy scored a fourth straight headed goal for the equaliser in the 72nd minute. Paul Scholes and impact sub Ole Gunnar Solskjaer then combined to play in Juan Sebastián Verón to make it four before Beckham got his much-deserved goal with minutes left on the clock to complete a 5-3 comeback win, highlighting  United’s never-say-die spirit. 


Man United 5-2 Spurs: Comeback Thriller (April 25, 2009)


United made another thrilling comeback against Spurs at Old Trafford in 2009, a pivotal result in their title-winning campaign. The Red Devils were battling bitter rivals Liverpool for the Premier League honour that season, so each game became a final. The Reds defeated them 4-1 at Old Trafford a month before Spurs visited them in April 2025, but their lead slipped, opening up an opportunity for Ferguson’s men. However, the Lilywhites proved tricky again, taking the lead through Darren Bent getting on the end of Vedran Ćorluka’s cross despite the hosts starting brightly. Before United could recover, they were down 2-0 minutes later with Luka Modric finishing Aaron Lennon’s cross at the far post. The Theatre of Dreams watched their team head down the tunnel with a multiple-goal deficit, hoping for another miraculous second half to rescue them not only in the match but also in the title race.                       


As unbelievable as it sounds, incredible at the same time, the Ferguson-led side managed to do so again, but this time with some controversy. On the hour mark, the Red Devils won a penalty out of nowhere when the official pointed to the spot, buying into Michael Carrick’s playing foul when Heurelho Gomes clearly got a touch on the ball, which Cristiano Ronaldo converted. There was no VAR technology back then to correct the obvious error. Once on the scoresheet, the Portuguese unleashed his full potential, assisting Wayne Rooney before putting United in front seconds later in front of a now euphoric home crowd, with the English forward returning the favour. The pair again combined as the red storm refused to cease, with Rooney completing his brace. Four goals in just 13 minutes and adding more salt to the wounds, ex-Tottenham striker Berbatov completed the scoring for the 5-2 victory, confirming another Spurs capitulation in the second half.     


Penalty drama (1 March 2009)


The league is not always the stage where both sides have produced some dramatic moments, but they also came in cup battles, especially in the 2009 League Cup final. Both clubs were on the edge of adding more history, with Manchester United chasing a three-peat in the campaign, with the League Cup being the first of that run, while Tottenham were looking to retain the trophy, which ended their nine-year trophy drought. However, the teams could not be separated in 120 minutes of football as both defences stood strong, making penalties inevitable. Tottenham were the defending champions, so the pressure seemed to creep in to them as they looked out of place in the shootout, as Vedran Corluka's successful effort between Jamie O'Hara's Foster-saved spot-kick and David Bentley dragging his shot wide was rendered meaningless as the Red Devils scored all four of their penalties in the 4-1 win. Spurs would have clinched Europa League football had they won, but Manchester United broke the reigning champions' hearts to clinch the title with a player-of-the-match performance from Foster. United completed a domestic double and beating Spurs proved crucial again.  


Spurs 2-0 Man United: Eriksen in seconds (January 31, 2018)


It is not always a dull and gloomy episode for Tottenham to remember in this fixture, as they started making their presence felt with Manchester United falling off from their elite standard post-Ferguson’s departure. Tottenham, under their transformative manager Mauricio Pochettino, invited United to Wembley, serving as a temporary home ground that season due to the new stadium being built, with both teams carrying good form. However, the Spurs had a swagger this time and were determined to correct their past wrongs in this fixture. They produced one of the best and exciting starts to the Premier League game with a goal just 10.54 seconds into the match. Harry Kane and Dele Alli combined well for Christian Eriksen to strike past De Gea for the fastest at the new Wembley and one of the quickest goals scored in Tottenham and Premier League history. Spurs' smile widened when Phil Jones turned his clearance into the back of the net from Trippier's dangerous cross to make it 2-0 on the evening that stayed until the end. Pochettino’s side beat a defence that kept six consecutive clean sheets leading up to the fixture by outshooting them 22-6 and establishing a new reign. 


Man United 1-6 Spurs: Rout (October 4, 2020)


In that loss, Jose Mourinho was in the Manchester United dugout, but two years later, he oversaw the Red Devils’ joint-heaviest Premier League defeat as Tottenham manager. The only relief for the home side was that there were no spectators at Old Trafford to witness the humiliation due to the pandemic in 2020 otherwise, the backlash would have been extreme. It was an early period in the campaign because of the delayed schedule, but nobody predicted the outcome of the game to be like that. It did not look at first that United would be at the end of such a thrashing when Bruno Fernandes converted a penalty within minutes of the game. 


However, everything went south for the hosts when their defensive fragilities, with Harry Maguire being the prime player behind the faults, were exposed by Spurs from time to time. 


Tanguy Ndombélé equalised in the fourth minute, capitalising on Maguire making a mess of his clearance, then pulling his own man down, who looked to rectify his error, before Heung-Min Son gave his side the lead in the seventh minute. Disaster struck when forward Anthony Martial was controversially sent off, leading to the visitors adding two more goals before halftime.


Harry Kane got into the act after Maguire was at fault again for not preventing a quick free-kick chance and Son completed his brace. It was the second time Spurs repeated the feat of scoring four goals at half-time at Old Trafford, but they weren’t done with it. Serge Aurier made it five five minutes into the second half, with Kane completing the rout from the spot in the 79th minute to give the visitors a memorable afternoon to celebrate. It was the biggest win Tottenham registered in this fixture at Old Trafford and the second time they put six past United in history. For the hosts, managed by former player Ole Solskjaer, it was one of their lowest points in the club’s history.   


Man United 3-2 Spurs: A hat-trick to savour (13 March 2022)


Despite failing to end their slump even after recalling the star man, Manchester United could still cherish some of the eye-catching moments Cristiano Ronaldo produced in his second stint with the club. One of those came against the Premier League team he has scored most often against, Tottenham Hotspur, in March 2022 under the lights at Old Trafford. Even at 37, the Portuguese football superstar showed the class that defines him, scoring a screamer for the opener, standing outside his box unmarked and unchallenged. Spurs made a good response going down and put the ball in the net through Ben Davies, but he was flagged offside. However, it did not take long for the equaliser as relentless pressure from the visitors earned them a spot after Dejan Kulusevski’s cross struck Alex Telles’s outstretched arm.


As often he does, Kane converted the penalty coolly, but his side failed to uphold it, going down again just two minutes later. Jadon Sancho's cross, following a brilliant run down the left, found an onrushing Ronaldo, who finished from close range with ease. Once again, Tottenham’s response going behind was apt, with Son drawing level again, but he dragged his shot wide from Kulusevski’s pass, the Swede being a menace for United’s defence. Spurs did draw level, although it came from the opposite flank with Son and Reguilon combining to force an own goal from Harry Maguire. However, nothing could have denied Cristiano from making a proper ‘Ronaldo show’ in the evening by rising high from an 81st-minute corner for a textbook header to complete a splendid hat-trick, his first in a United shirt since 2008, giving the Red Devils a thrilling 3-2 victory.

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