Tottenham Hotspur welcome Manchester United to north London on Sunday for a Premier League clash that, in the not-so-distant past, would have been a top-of-the-table encounter.
However, this season, it’s a bottom-half affair. Instead of vying for European football, both sides will be battling to distance themselves from the relegation zone.
With United in 13th on 29 points from 24 games and Spurs in 14th with 27, it’s safe to say it’s been a poor season for both teams.
For the Red Devils, off-field upheaval, poor recruitment and a lack of quality on the pitch seem to be the culprits. Meanwhile, Spurs have had their own struggles, with injuries playing a significant role in their poor campaign as manager Ange Postecoglou has been constantly losing key players like Micky van de Ven, Cristian Romero and Dominic Solanke week after week.
Postecoglou’s job is certainly under pressure, but a win over United could ease that tension, even if just for a week or two.
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He’ll be hoping his side can replicate some of their best-ever results over United, 10 of which we’ve recounted here.
10 Tottenham 4-1 Man Utd 1995/96, Premier League
Tottenham mostly had a forgettable season in 1995/96, finishing 8th in the Premier League, and crashing out of the League Cup and FA Cup in the third and fifth rounds respectively.
Perhaps the highlight, however, was their 4-1 thumping of would-be champions Manchester United at White Hart Lane on New Year’s Day in 1996.
Teddy Sheringham, who would later join United in 1997, opened the scoring on the day, while Sol Campbell and Chris Armstrong, who scored a brace, were also on the scoresheet.
9 Tottenham 3-1 Man Utd 2000/01, Premier League
Manchester United had already been crowned Premier League champions when they travelled to White Hart Lane in May 2001.
Clearly having taken their foot off the gas after defeats to Derby County and Southampton, they slumped to another loss against Spurs, who were more than happy to take advantage of their complacency.
While not a classic in the traditional sense given that nothing was really on the line, Willem Korsten’s opening goal – chesting the ball down on the edge of the box before volleying it over United goalkeeper Raimond van der Gouw – was arguably one of the best Spurs have ever scored against the Red Devils.
8 Man Utd 0-3 Tottenham 2018/19, Premier League
Tottenham started the 2018/19 Premier League season in fine form, winning their first three games, the last of which was a commanding 3-0 victory over Manchester United.
After a goalless first half, Harry Kane broke the deadlock in the 50th minute, before a brace from Lucas Moura sealed the win for Mauricio Pochettino’s side.
However, Spurs’ bright start came to an abrupt halt a week later when they suffered a 2-1 defeat to Watford at Vicarage Road.
7 Tottenham 3-1 Man Utd 1998/99, League Cup
En route to winning the League Cup in 1998/99, Tottenham had to overcome Manchester United in the quarter-finals. United, sitting 2nd in the Premier League, were heavy favourites against Spurs, who were struggling in 12th place at the time.
However, a brace from Chris Armstrong and a stunning long-range strike from David Ginola, who tormented United’s defence that night, secured a memorable 3-1 victory.
With United securing a treble, Spurs were the only side to stop the Red Devils in this particular season with this win.
6 Tottenham 4-3 Man Utd 2024/25, League Cup
In a modern-day Spurs-United clash in December 2024, Ange Postecoglou’s side triumphed 4-3 over Ruben Amorim’s Manchester United in the League Cup quarter-finals.
Spurs raced into a three-goal lead with a Dominic Solanke brace and a goal from Dejan Kulusevski, before United fought back through goals from Joshua Zirkzee and Amad Diallo after some calamitous defending.
Son Heung-min made it 4-2 late on, but veteran United defender Jonny Evans headed home in injury time to set up a nervy finish. Spurs held on to secure the win, setting up a semi-final clash with Liverpool, where they were beaten 4-1 on aggregate.
5 Tottenham 4-0 Man Utd 1986/87, First Division
Back in the late 1980s, Tottenham were the superior side to Manchester United, who were still finding their feet under Sir Alex Ferguson.
The Lilywhites made their superiority clear when the two teams met in the First Division in May 1987, running out as comprehensive 4-0 winners thanks to a brace from Mitchell Thomas and goals from cousins Paul and Clive Allen.
Spurs finished the season in third, while United ended up in 11th.
4 Tottenham 3-1 Man Utd 1961/62, FA Cup
Tottenham won the FA Cup in 1960/61 and looked poised to repeat the feat the following year when they faced Manchester United in the semi-finals.
In front of 65,000 fans at Hillsborough, the Lilywhites put on a stunning display, thumping the Red Devils 3-1, with Jimmy Greaves, Cliff Jones and Terry Medwin all finding the net for Bill Nicholson’s side.
Spurs went on to defeat Burnley by the same scoreline in the final, securing back-to-back FA Cup triumphs.
3 Manchester United 2-3 Tottenham 2012/13, Premier League
When Tottenham travelled to Old Trafford in September 2012, the Lilywhites hadn’t beaten Manchester United in any competition in over a decade, with their last win coming back in May 2001.
However, an early goal from defender Jan Vertonghen set the tone for change, before a second from Gareth Bale seemed to seal it.
After the break, there were three goals in three minutes. United pulled one back through Nani and Clint Dempsey extended Spurs’ lead before Shinji Kagawa made it 3-2.
United pushed for an equaliser, but Andre Villas-Boas’ side held firm.
2 Tottenham 2-1 Man Utd 2016/17, Premier League
Tottenham bid farewell to White Hart Lane in style, capping their most successful Premier League season to date with a 2-1 victory over Man Utd in the famous ground’s final game.
Victor Wanyama scored early on before Harry Kane’s finish just after the restart put Mauricio Pochettino’s side in cruise control. Wayne Rooney would score the final goal at the old stadium but that did little to dampen the home team’s spirits as they celebrated finishing second in the table – above Manchester City and Arsenal.
Spurs moved to Wembley the season after, though they are yet to top their 86-point haul from 2016/17, where they remained unbeaten at home and finished above rivals Arsenal for the first time in over 20 years.
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In one of the most iconic Tottenham displays of recent times – and certainly their best against United – Spurs dismantled Ole Gunnar Solskjaer’s side at Old Trafford in October 2020, hammering United 6-1.
United took the lead with an early Bruno Fernandes penalty, but from that moment on, it was all Tottenham.
Tanguy Ndombele started the rout, before two goals apiece from Harry Kane and Son Heung-min, plus a rare strike from defender Serge Aurier, sealed a momentous victory for the Lilywhites.