Tottenham 3-5 Manchester United, 2001
Spurs were in dreamland midway through this meeting at White Hart Lane, having established a 3-0 lead over the reigning champions thanks to goals from Dean Richards, Christian Ziege and Les Ferdinand.
Yet United proceeded to launch one of the most famous comebacks of the Alex Ferguson era. Andy Cole narrowed the deficit early in the second half before Laurent Blanc cut it further in the 58th minute. Ruud van Nistelrooy restored parity soon after, then Juan Sebastian Veron and David Beckham completed a sensational turnaround.
Manchester United 2-3 Tottenham, 2012
Prior to this clash in September 2012, Tottenham were without a win at Old Trafford since 1989. They also arrived in Manchester on the back of a mixed run of form; while Andre Villas-Boas’ men had recently beaten Reading and Queens Park Rangers, they began the campaign by taking two points from a possible nine against Newcastle United, West Bromwich Albion and Norwich City.
A Jonny Evans own goal gave the visitors the lead within two minutes, and Gareth Bale doubled their advantage shortly after the half-hour mark. Nani hit back in the second half, before Clint Dempsey made it 3-1, meaning Shinji Kagawa’s goal was nothing more than a consolation.
Tottenham 4-1 Manchester United, 1996
Tottenham began 1996 in the perfect fashion, thrashing Alex Ferguson’s side on New Year’s Day. Teddy Sheringham opened the scoring against his future employers, but United equalised almost immediately through Andy Cole.
Spurs’ advantage was restored on the stroke of half-time, though, as Sol Campbell edged them back ahead. A Chris Armstrong double then wrapped up the points after the break, although the defeat ultimately did not prove decisive for United, who went on to win the title by four points.
Manchester United 2-1 Tottenham, 1999
Manchester United made history by winning the Treble in 1998/99, although it is well known that they required a dramatic late comeback to overturn a 1-0 deficit against Bayern Munich in the Champions League final. Their margin of victory was also narrow in the Premier League title race, as the Red Devils finished just a solitary point clear of Arsenal.
Both teams had a chance of finishing on top heading into the final day, but it was United who had their fate in their own hands. They duly delivered, beating Tottenham 2-1 at Old Trafford to the delight of both sets of fans, with the visiting supporters keen to avoid helping Arsenal win the league.
Manchester United 5-2 Tottenham, 2009
Just a few weeks after beating Tottenham on penalties to win the League Cup, United registered a more emphatic triumph against the north London outfit in the Premier League.
Spurs actually went 2-0 up thanks to quick-fire goals from Darren Bent and Luka Modric in the first half, but United roared back and ran riot after the interval. A Cristiano Ronaldo spot-kick got them back in the match, before a Wayne Rooney brace and another Ronaldo effort suddenly made it 4-2 within the space of four minutes. Dimitar Berbatov then put the game beyond his former club by striking in the 79th minute, leaving Spurs to rue another loss to the Red Devils.
Tottenham 3-0 Manchester United, 2016
Tottenham fell away soon after this comfortable defeat of Manchester United in April 2016, but they were still in the Premier League title tussle following this resounding triumph. Mauricio Pochettino’s men were magnificent in front of their own fans at White Hart Lane, as goals from Dele Alli, Toby Alderweireld and Erik Lamela swept United away to move Spurs to within seven points of league leaders (and eventual champions) Leicester.
This defeat proved costly for United, who ultimately missed out on the top four on goal difference after finishing level on points with Manchester City.