Manchester United: United's 10 Worst Defeats in the Premier League Era

The past three months have thrown up three shocking defeats for Manchester United; the 6-1 mauling by Manchester City at Old Trafford, Crystal Palace's impressive 2-1 victory in the League Cup and FC Basel's 2-1 Champions League win that saw United dumped out of Europe's top competition.

Fans may be inclined to look upon these recent weeks as the end times for Fergie and their club's domestic dominance but the truth is, Sir Alex and United have been here before.

United's greatest hours have been comebacks in one form or another, and as history inevitably repeats itself, fans and rivals alike would do well to review the club's most painful defeats in their recent history.

We all know about the 6-1 and the two recent cup defeats at home and abroad, so here are United's 10 worst defeats in the Premier League era from past seasons. Enjoy.

Manchester City 4, Manchester United 1: 14th March 2004

Before the living nightmare of October's 6-1, Man City had previously failed when it comes to scoring big against their bitter crosstown rivals.

In 1989, City famously humiliated United in a game that is still fondly remembered within the folklore of club and supporters alike today. 5-1 was the score.

Unfortunately that day lies just beyond the reaches of 1994 and the Premier League era, and therefore not eligible for inclusion on our list. City do however have another match day to hoist aloft in its absence: 14th March 2004.

Coming just a week after United had been dumped out of the Champions League, City piled on the pain with a side packed full of ghosts from their red rival's past.

Kevin Keegan, former Liverpool player and Newcastle boss, stood in the dug out. Of the goal scorers, Robbie Fowler and Joe Macken were an ex-Liverpool legend and former United trainee respectively. City's side also included ex-Liverpool red, Steve McMananman.

This was no rubber either. After their 4-1 thump of a defeat, United found themselves 12 points adrift of league leaders Arsenal with just ten games remaining. A points lead that was all but unassailable in the wake of their humiliating defeat.

Newcastle United 5, Manchester United 0: 20th October 1996

Speaking of Kevin Keegan, this 5-0 victory over Manchester United at St. James Park is perhaps his finest hour as a Premier League manager.

Whilst Newcastle would go on to implode in the run-in, before Christmas the Toon Army looked set to continue their rampant charge to the title, which was helped by this early season rout of their major rivals, Manchester United in October. Roberto Mancini take note.

The scoring opened with a controversial Gavin Peacock header. Manchester United argued the ball hadn't crossed the line but the referee awarded the goal, a decision that was later vindicated by video replay.

Even without comparison, Newcastle's second was an utterly conclusive wonder-strike from David Ginola, who fired home from just outside Schmeichel's box, hitting his shot across United's goalkeeping legend.

Two more were scored by Les Ferdinand and Alan Shearer, but the best was yet to come as Newcastle's defensive rock of the day, Philippe Albert, stormed upfield to float a ball over United defence. It was a finish of pure quality and magic, all the more impressive considering it came from a Magpie centre-back!

Chelsea 5, Manchester United 0: 3rd October 1999

Coming off the back of their treble winning season, United held a 29 game unbeaten run in the Premier League. That was all to change when the Reds visited Stamford Bridge in the October of 1999.

Massimo Taibi has become a figure of fun, fear and ridicule both within and without Old Trafford but at the time, in the wake of Peter Schmeichel's departure, the Italian keeper was a £4.5M replacement to the Great Dane, a price that meant a lot more then than it does today.

The match didn't start well for United. A Taibi error gifted the ball to Chelsea, with Gus Poyet bursting through from midfield to slot home an early opener.

Following a red card for Nicky Butt, United capitulated in the face of a Chelsea oozing with form and swagger in front of their home crowd. With goals from Chris Sutton, a second from Poyet, a Henning Berg o.g. and one from Jody Morris, United crumbled to their largest Premier League defeat, a scoreline that would not be topped until City's Old Trafford heroics earlier this year.

This was Taibi's fourth and final game for Manchester United, a run in which he conceded a shocking 10 goals. His services were not maintained.

Manchester United 1, Liverpool 4: 14th March 2009

The 2008/9 season saw Liverpool emerge as United's main title rivals for the season. It was perhaps the closest the club had come to lifting a league title in some years, creating an intensity that only added to the animosity, rivalry and competitive hunger that simmered between England's two historical footballing powerhouses.

It was a season that will probably be best remember for Rafa Benitez's Keegan-esque 'facts' meltdown in January, but another piece of football pop culture myth and legend was born later in the month of March.

With United holding the advantage in the title race going into the potential league decider derby, the Premiership showdown on 14th March 2009 was a must win for Gerrard and Co.

First blood was to United. Pepe Reina brought down Park Ji-Sung in the area to allow Cristiano Ronaldo to convert from the spot to give his team an early lead.

It wasn't to last however, as Fernando Torres hounded Nemanja Vidic into a mistake he then capitalised on. This was a trend that would embolden the match on the Spanish striker's highlights reel, as he tormented the Serbian defender relentless throughout the match until his sending off for hold back Steven Gerrard, receiving a second yellow and his marching orders.

Even before Vidic's sending off, Gerrard had added a second from the spot, but with United's defensive rock out of the game, Liverpool romped home to make it 4-1 at Old Trafford. To their credit, Liverpool won the game in style, topped off by a superb third goal courtesy of a Fabio Aurelio free kick and Andrea Dossena's beautiful lift over Edwin Van Der Sar, reminiscent of Philippe Albert's effort back in 1996.

With United still holding a four point lead in the title race and a game in hand, even a Liverpool victory of this magnitude didn't turn out to be the decider the result suggests it could have been. It was still a sickening sight for United fans who had to watch their team humiliated at home by their greatest rivals.

Southend 1, Manchester United 0: November: 7th November 2006

It may have only been a Carling Cup match, but following Sir Alex's celebration of 20 years in charge at Old Trafford, United headed down the M1 to face Southend with 10 recognised internationals in the starting line up.

Cristiano Ronaldo, Wayne Rooney, Darren Fletcher and Gabriel Heinze were all included in the first eleven, but it was Southend's keeper Darryl Flahavan and their cult striker, Freddy Eastwood, who were the game's match winners.

Flahavan put in a sterling performance between the sticks to deny United's super stars up close and from long, whilst Eastwood curled in a peach of a free kick to earn the Championship club an unlikely league cup victory.

Not only was it a loss against a team of relative minnows struggling in their own division, but it was a game that probably could of, and should of been won on any other day.

The amount of shots United had on Southend's goal, including some nerve jangling smashes on the woodwork from Dave Jones in particular, rounded off a frustrating and humbling night for Sir Alex and his team.

Manchester United 0, Leeds United 1: 2nd January 2010

After Liverpool, Leeds are, to some, Manchester United's most bitter rivals in the English game, especially prior to the arrival of Sheikh Mansour.

United had never before lost an FA Cup third round tie or suffered the ignominy of being knocked out by a lower-division side during Sir Alex Ferguson's tenure as manager. Not since a shock defeat to Harry Redknapp's Bournemouth in 1984 had the club found themselves on the wrong end of such a fixture.

To say that Leeds arrived at Old Trafford as underdogs is an understatement. Regardless of the ferocious rivalry between the two clubs, the supposed gulf in class was assumed to be enough that United could coast to a comfortable victory against their Yorkshire foes.

Perhaps it was complacency or arrogance, but United were lacklustre from kick-off, unable or unwilling to compete with the same intensity as their tenacious opponents.

Jermaine Beckford was the visitor's hero, bringing down a sublime ball from Johnny Howson on the half-way line to outpace the United defence, enjoying a fortunate scuffed finish to earn his side a much deserved winner.

Losses to lower league terms is never acceptable for a so-called super club, especially when the victors are regional rivals of the highest order. A grim day for the Old Trafford faithful.

Manchester United 0, Fenerbahce 1: 30th October 1996

Before the visit of Turkish champions, Fenerbahce, Manchester United had not been bettered at Old Trafford by foreign opposition in all their history, with a spotless record at home stretching back to 1956.

Records are there to be broken however, and Elvir Bolic’s match winning goal was a jaunting full-stop in the United history books.

As much as the home side tried they just couldn't haul themselves back on level terms. Eric Cantona especially wilted on the night with a number of botched chances and harmless attempts off target.

Sir Bobby Charlton looked on from the stands as United's proud European tradition tumbled to an inevitable but gutting conclusion.

Southampton 6, Manchester United 3: 26th October 1996

Just one week on from their 5-0 defeat at Newcastle, United would again be pulled apart on an away day trip to the other side of the country.

Heading south this time, United were taken to pieces by two inspired hat tricks by Mat Le Tissier and Egil Ostenstad, along with a sending off for Roy Keane.

The match was a quintessential 90's goal orgy, with caution thrown to the wind to favour of manic attacking football. The action came thick and fast right up to the match's dying moments, with four of the goals scored coming in the last ten minutes.

The 6-3 was an undeniably enjoyable spectacle in terms of pure, brainless footballing glee, but such a scoreline stuck in the necks of United fans, especially those who had made the long trip down to the southern coast expecting a fairly comfortable victory.

Following on from the rout at St James Park a week earlier, it was a painful fortnight for supporters from the red side of Manchester.

York City 4, Manchester United 3 (agg): 20th September, 3rd October 1995

It was the stuff of fairytales. York City, at the time a struggling League 2 team headed west to Old Trafford, bagging themselves an unlikely 3-0 victory against a United reserve side.

The return leg was set to be 90 minutes of terrible retribution from a full strength first eleven desperate to save their blushes. United would go on to win the Premiership and FA Cup double, but against York City at home, they came unstuck.

Reinforced, United scored three; a brace from one young Paul Scholes adding to Terry Cooke's opener. York City managed to pull one back however, winning the tie 4-3 on aggregate.

Whilst tripping up against a motivated, lower league side with a team of reservists is somewhat explainable, perhaps even understandable, failing to set the record straight with a full-strength team that included Eric Cantona, Roy Keane and Andy Cole was inexcusable.

Barcelona, the Champions League Final 2009 and 2011.

Whilst Manchester United have suffered heavy and unexpected defeats, as evidenced by this list, no team has dented the club's ambitions, momentum and self-esteem in the way Barcelona have with their two recent Champions League final defeats.

The first, a 2-0 loss at Rome's Stadio Olimpico in 2009, was a startling display of dominance by the Catalan wizards, whose performance bamboozled Michael Carrick in the centre of United's midfield to the extent that he's never really quite recovered.

Manchester United, a club with the finest record in Europe, looked off-the-pace and extremely second rate against a Barcelona side who would go on to win everything they played for in Pep Guardiola's first year as coach.

The second final defeat was last season's 3-1 finale at Wembley, London. United seemed more prepared and ready for what they were about to face. Alas, they still couldn't come close.

After starting brightly, and replying to Barcelona's opener with a glorious, second half goal by Wayne Rooney, Barcelona kicked their play up another gear, pulling United to pieces in one of the greatest tournament final performances in recent times.

Both games were earth shattering wake up calls for both Manchester United's fans and the club itself. Whilst the scorelines may not have matched the hyperbolic heights of 6-1 or 5-0, the performances in both matches by Barcelona were acts of wilful domination and consumate control.

Being second best in Europe to possibly one of the greatest teams ever may soften the blows for some United fans, but for Sir Alex Ferguson himself, searching for that elusive third European title, or an immortal fourth, both losses were ambition breaking sucker punches.

Dishonorable Mentions

Manchester United 0, Coventry City 2: 26th September 2007

After a healthy 2-0 win against Chelsea, Sir Alex rotated his squad to give youth a chance. Unfortunately, Nani, Gerard Pique and Anderson fluffed their lines as Coventry City's Michael Mifsud scored an unlikely brace to deny the league leaders progress from the Carling Cup third round.

Benfica 2, Manchester United 1: 26th September 2005

Six years ago and it was again Benfica breaking United hearts in Europe. 2005 would see Sir Alex's side finish bottom of their group and crash out of Europe early on. It was an embarrassingly immature conclusion for a team also struggling domestically. Of course they would go on to lift the Champions League trophy three years later in Moscow against Chelsea, but such glories seemed impossibly remote in the darkest days of 2005.

Wolves 1, Manchester United 0: 17th January 2004

In a match United dominated, a fluke Kenny Miller goal secured the three points for Wolves. For the entire 90 minutes, United could do anything but score a goal leading to one of the most excruciatingly frustrating results in their recent history.

Manchester United 0, Borussia Dortmund 1: 9th April 1997 

Emotions ran high in the run up to the club's first ever Champions League semi-final against Borussia Dortmund. Whilst the red half of Manchester geared itself up for glory, Lars Ricken had other ideas, firing home to give the German side an important first leg away win. Cantona was particularly wasteful in front of the opposition goal, squandering a number of chances. United lost the reverse fixture by the same result and were knocked out of the competition.

Manchester United 0, Portsmouth 1: 8th March 2008

By the end of this FA semi-final, Rio Ferdinand would be standing in as goalkeeper after a Tomasz Kuszczak red card. Sulley Muntari converted the ensuing penalty past Ferdinand as Portsmouth crept into past United and into the final.