Liverpool vs. Manchester United: The eight greatest matches of the historic Premier League rivalry

Welcome to Benge’s Premier League Table. Every week James Benge will be ranking something, anything, in the Premier League, breaking down everything from the nerdiest tactics to the best kits, to the worst haircuts. This week, he assesses the most likely winners of individual awards come the end of the season.

Manchester United and Liverpool is as intense a rivalry as any in the English game. An enmity between two cities, ignited by the opening of the Manchester Ship Canal in 1894, which robbed Liverpool’s Merseyside docks of significant port fees, has been played out on the football pitch in exhilarating fashion by the two most successful teams in this country’s history.

“As a young United fan growing up at the time that I did, it was just a fact that you didn’t like Liverpool Football Club,” Gary Neville said in 2018. “You didn’t want them to win a game, never mind a trophy… The very first thing that any Manchester United player should have explained to them when they join the club is that it’s unacceptable to lose to Liverpool, but also that there’s no feeling to rival beating them.”

Sunday’s meeting between the two could be as significant as any of the games Neville or anyone else has played in. United, yet to seriously compete for the title since Sir Alex Ferguson’s departure in 2012, hold a three point lead over Jurgen Klopp’s reigning champions as the domestic season approaches its halfway juncture. That these two could be serious contenders for the championship is a rare sight indeed, perhaps the 2008-09 season is the only in the Premier League era where these two great rivals have been involved in a title race.

When one of these teams waxes the other wanes. The great glories of the 1970s and 80s for Liverpool were rather more barren times for United whilst Ferguson fit 13 of the Red Devils’ record 20 league titles into the 30 year barren run at Anfield.

And yet this rivalry has produced plenty of classic matches. Below we rank eight of our favorites.

8. Bye bye Mourinho

Liverpool 3 Manchester United 1, Premier League, December 16, 2018

There have been better games than this and moments where there have been hints of a power shift but few games have so decisively made the case for one team being so far ahead of their great rivals. It is curious that it should be a game where Manchester United were level with Liverpool for 64 minutes but in truth they were clinging on for dear life throughout this contest.

An uncharacteristic error from Alisson gave Jesse Lingard the chance to draw the visiting United side level but it was one of only two shots on target Jose Mourinho’s side managed in a game where they had tried to match Liverpool’s technical excellence with muscle and physicality. For a time they resisted the Reds front three but the introduction of Xherdan Shaqiri swung the contest in favor of Klopp’s side.

This would be the game to make plain the chasm between these two sides, one that had grown on Mourinho’s watch and cost him his job the following day. As for Klopp, he has not lost to United since.

7. Dimitar Berbatov’s star role

Manchester United 3 Liverpool 2, Premier League, September 19, 2010

In a curiously unremarkable season this was a thrilling contest. It had little bearing on the end of season shakeout, United won the league at a relative canter whilst Roy Hodgson proved to be a disastrous fit for a Liverpool club that were about to be freed from their disastrous owners Tom Hicks and George Gillett.

Instead this game was an ode to Dimitar Berbatov, never quite as loved at Old Trafford as he was during his time with Tottenham at White Hart Lane but always welcome in Manchester for his brilliant hat-trick on this day. A stooping header in the first half was followed by a genius overhead kick in the second, the sort of diffident genius that typified the Bulgarian at his best.

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Perhaps this win was all the sweeter for the Old Trafford faithful because it looked like Steven Gerrard might prove to be Liverpool’s hero when a penalty and free-kick drew them level only for his efforts to be in vain as Berbatov’s header six minutes from time earned Sir Alex Ferguson’s side a famous win.

6. European union

Liverpool 2 Manchester United 0, Europa League, March 10, 2016

One might have assumed that these two stalwarts of English and European football might have crossed paths before 2016 but this was their first, and so far only, meeting in continental matches. A round of 16 tie in a second tier competition hardly seems an appropriate venue for such an intense rivalry to play out but the ties themselves were engrossing, and a significant staging point in Liverpool’s development under Klopp.

It was at this stage in the German’s first season at the club that his players began to show the intense energy that was their manager’s hallmark and it proved far too much for the more considered, possession-oriented United of Louis van Gaal.

There were even a few hallmarks of Klopp’s future in Roberto Firmino dropping deep to slip through the overlapping right-back Nathaniel Clyne to win a penalty. The Brazilian then scored the second, dovetailing excellently with an inside forward in Daniel Sturridge who on that night looked like the player Liverpool would eventually find in Mohamed Salah.

5. Spice Boys sizzled

Liverpool 0 Manchester United 1, FA Cup Final, May 11, 1996

In football terms this was certainly not vintage fair but for United it did serve as a valuable check on their rival’s building momentum to rob them of the FA Cup and shine a harsh spotlight on a team that seemed to be getting carried away with itself before living up to the standards expected of it.

This was, of course, the famous Spice Boys final where Steve McManaman, Robbie Fowler et al arrived in white Armani suits, a sight that prompted Ferguson (still some way from his knighthood) to immediately tell assistant Brian Kidd his side would win the game 1-0. They did. Eric Cantona produced the sole quality moment of a drab contest with his 85th minute volley.

“I think that’s arrogance or over confidence or I don’t know,” Ferguson said years later. “It was ridiculous.” Liverpool players themselves would agree now, with Neil Ruddock subsequently claiming that the attire was the reason they lost the final. True or not it did reflect a team that had seemingly become too preoccupied with matters off the pitch.

4. United’s treble journey

Liverpool 1 Manchester United 2, FA Cup fourth round, January 24, 1999

At the time Liverpool could not have known what United would go on to achieve in the following months of the season but as if a first FA Cup win over their great rivals since 1922 was not motivation enough, this would have retrospectively gone down as the day when they robbed United of the treble.

Until the 88th minute it seemed a Liverpool win was on the cards. Michael Owen had headed in an early opener for United and Paul Ince came back to haunt his old side by clearing Roy Keane’s header off the line, preventing an equalizer. The Irishman was at his dynamic best that afternoon, forcing a superb save from David James, hitting a post and winning the ball whenever it came near to him, yet it did not seem like it would be enough.

Still this United team would overwhelm you with numbers, as they did from Beckham’s free-kick as full time beckoned, with Andy Cole knocking a header into the path of Dwight Yorke to tap in at close range to level the match. As Old Trafford boomed out its support, the winner came in similar fashion though this time it was Paul Scholes knocking the ball down and Ole Gunnar Solskjaer striking.

There would be twists and turns aplenty for United over the remainder of that season but this game crystallized a refusal to admit defeat that would serve them well on the bigger stage in the Nou Camp several months later.

3. United go down fighting

Liverpool 3 Manchester United 3, First Division, April 4, 1988

In truth, United would probably never have caught Liverpool at the top of the First Division even if they had won at Anfield. Liverpool were 11 points clear with just under a month of the campaign to go and in the late 1980s were not the sort of team to let those leads slip. For a moment you might have wondered if Ferguson might be about to mastermind a remarkable end to the campaign when Peter Davenport beat Alan Hansen to cross low for Bryan Robson to score the opener.

But Liverpool seemed to swiftly eliminate that hope with a trio of exceptional goals in a superb display of attacking football either side of half-time. Peter Beardsley, Gary Gillespie and Steve McMahon netting before Colin Gibson saw red for United. Then came one of those rallies from Ferguson’s side that would go on to be immortalized in Old Trafford history. Robson drew them back within one with a deflected strike from outside the box before Gordon Strachan darted up from nowhere in the 78th minute to slot past Bruce Grobbelaar, lighting up an imaginary cigar to infuriate Anfield even more.

This game may not have changed much or redefined the rivalry but it was an incresibly fun football match.

2. Torres, Vidic and that Gerrard celebration

Manchester United 1 Liverpool 4, Premier League, March 14, 2009

Considering that this was another game that ultimately had little bearing on the title race it is perhaps curious that it has so indelibly written itself into the history of the Premier League. This was not the rebirthing moment of a new Liverpool nor a game to end Manchester United’s dominance of England. It was just a ludicrously fun game and a moment where the visitors believed they might end their 20 year title wait.

From the seventh minute it was apparent that Fernando Torres had the number of the United backline, and that his pace was more than Nemanja Vidic could dream of coping with. Even Cristiano Ronaldo’s early penalty did not put the Spaniard off his stride, moments later he was picking Vidic’s pocket and chipping the ball over Edwin van der Sar as if these weren’t the best center back and goalkeeper in the world.

Steven Gerrard celebrates his goal in Liverpool’s 4-1 win over Manchester United at Old Trafford in 2009 Getty Images

If that was one flashbulb moment in this derby, the other would come just before the half when Gerrard won a penalty that he emphatically converted. There was no moment that more typified the jubilation that was suddenly engulfing the red half of Merseyside than their captain fantastic kissing the badge, his eyes gazing into the camera ahead of him as he ran to plant one on the television screens of viewers around the world. Liverpool, it seemed, were back. Stunning goals by fullbacks Fabio Aurelio and Andrea Dossena put the final touches on a performance that humiliated United on their own ground.

It was a propulsive result for Liverpool, whose only dropped points in the final nine matches of that season came in a 4-4 draw to an Andrey Arshavin-inspired Arsenal at Anfield. Unfortunately the scale of that humiliation would rouse United as well, who after defeat to Fulham in the following game matched Rafa Benitez’s side near blow for blow to ensure that they held on to the title.

1. United deny Liverpool the treble

Liverpool 1 Manchester United 2, FA Cup Final, May 21, 1977

This is a stand out moment in United’s history for so many reasons. It wasn’t just a first FA Cup Final win over their great enemy but one that came a year after Tommy Docherty had promised his side would make amends for the shock defeat to Southampton. “We’ll be back next year and this time we’ll win it,” had been his promise to supporters filing Manchester’s Albert Square.

To do so they would have to beat a Liverpool side who had defeated them earlier that month on their way to the First Division title. Perhaps the upcoming European Cup final against Borussia Monchengladbach was preying on their mind but Bob Paisley’s side were a winning machine within touching distance of their first treble. Certainly it took Stuart Pearson’s excellent volley to wake them out of their torpor with Jimmy Case twirling and volleying home two minutes later. Parity lasted no longer than United’s lead before Lou Macari shanked a volley onto team-mate Jimmy Greenhoff’s chest, a bizarre way to win a spectacular match.

Four days later Liverpool would get their hands on the European Cup, a salve at the time but 22 years on this victory would become all the sweeter for United. They had become the first English team to win the treble and it was only because of the underdog heroics of Pearson, Greenhoff et al that Liverpool hadn’t beaten them to it by several decades.