Manchester United vs. Chelsea: 10 Games to Define Rivalry Before Sunday's Match
With Chelsea sitting in fourth place in the league and 13 points back of leaders Manchester City, any dim hopes of climbing to the top will start this Sunday as the Blues host Manchester United. United are currently in second, three points behind their neighbors, and need the full lot to keep pace.
While the circumstances suggest that United would make much more of the points than Chelsea, neither side will bow down as the past decade has seen this rivalry blossom into one of the best in the entire league.
In the past seven seasons, the crown winner has been either wearing blue or red, as United hold a slight edge over the Chelsea with a 4-3 advantage in that window. And while the likes of Liverpool and Arsenal have found it difficult to remain relevant in the Premier League race, Chelsea have become one of the biggest names in world football and United canonized their place as the most successful club in English history.
There have been many great games between the two clubs over their centennial-plus histories that have come to make this a great matchup on Sunday. Here is a look at 10 of the very best in my opinion.
This list leans toward a Chelsea bias since it is what I know, but takes into account more than just results. It is an essentially revisionist look at how certain games are understood in hindsight and how those matches make Sunday's game all the more anticipated.
I am sure there are plenty more that I missed, so please, I encourage you to share your thoughts on this list and add any others you think are worthy.
Chelsea 5-0 Manchester United (Premiership: 03-10-1999)
1 of 11A seemingly meaningless game if you look at each team's results on the season. Manchester United would get over the heavy defeat by going on to win the league by 17 points and for the sixth time in eight years. Chelsea would finish a disappointing fifth place after coming off a third-place finish the previous year and add some talent to the squad.
But if you look at it in the context of just the two clubs themselves, it takes on a bit more meaning.
The biggest win by Chelsea over United was somewhat of a turning point in the paths these two teams would take.
Going into the match Chelsea were winless in 15 out of the last 16 the two sides had played. United on the other hand were by far the best side in England and challenging in Europe as well. Following the match, the score began to even out between the two sides with Chelsea improving to 8-4-4 over the same number of games.
Though Ferguson’s United remained as strong as ever in the league, Arsene Wenger’s Invincibles of Arsenal were on the rise and nipping at their heels and Chelsea was about to undergo the Russian revolution of London which would see them enjoy their first bits of success.
So while Gustavo Poyet’s goal inside the first 30 seconds did not directly set in motion a chain of events that would ultimately lead this rivalry to the one it is today, it did give the club a boost to know that the domination the Red Devils enjoyed for so long was over for good.
Manchester United 4-0 Chelsea (FA Cup Final: 14-05-1994)
2 of 11Most Chelsea fans would probably do better to forget this day altogether, but in hindsight it wasn’t all that bad.
Going into the match, few if any expected Chelsea to come away with a win. The Blues had made a somewhat remarkable run to the final as their results in the earlier rounds (winning only one game by more than two goals) reflected the mediocrity this squad really was.
On the other hand, United was essentially a team of all-time greats.
(Just look at the picture above of the starting lineups.)
And while the final score line is representative of everything I have said up to this point, the actual contest itself was not. Chelsea held this incredible front line and midfield in check for 60 minutes and actually were the better team in the first half.
However, two penalties in the space of six minutes, which Eric Cantona notoriously put in the same exact spot, was too much for the Blues to overcome and they would fall 4-0.
However, despite the result, Chelsea showed a resilience that would come to be their moniker for the next decade. Their first major final in over 20 years did not get them the result they hoped for, but did establish them as a power on their rise to the top.
Chelsea 2-1 Manchester United (Premiership: 26-04-2008)
3 of 11Chelsea were three points back of United in the league heading into this late-season match. A win kept them in the title race with two matches to go, while anything less all but surely eliminated them.
United entered the match knowing that the likes of Didier Drogba, Michael Essien and John Terry were all in top form and that to win the game they must beat them. However, it turned out that the player they really needed to stop was one German by the name of Michael Ballack.
Ballack was sensational on the day, scoring both goals that kept Chelsea’s title hopes alive. People debate whether he ever lived up to the hype after he was picked up on a free transfer from Bayern Munich, but on this day there was no arguing his talents.
The match itself was one of the more heated contests in the rivalry. Tensions were as high as can be as Chelsea were no longer just some team, but had firmly established themselves as contenders with United. The Red Devils went into Stamford Bridge riding a six-game winless streak at the stadium, all a part of the historic run Chelsea would play without a loss at home to any side.
At the close of the season, the result mattered little as United won the league, but it was the first game in sometime where the teams knew that their paths would meet again—and it would not go as smoothly.
The 2007-08 season may have been the best in terms of the rivalry between these two sides as it would culminate in a great Champions League final. But it all started here at this game.
Oh yeah, did I forget to mention that the match itself was eclipsed by a postgame brawl between Patrice Evra and the Stamford Bridge groundstaff?
Chelsea 1-0 Manchester United (a.e.t) (FA Cup Final: 19-05-2007)
4 of 11It’s not easy for a 1-0 game where the only goal came 116 minutes into the match to make it on a list of the best in this rivalry. While defense is the foundation of their many championships, it has been their awesome ability to score goals that has made them so compelling.
However, there are a few things that made this matchup worthy of notice.
First off, this was the first FA Cup to be played at the new Wembley. While that may not mean much beyond a simple trivial fact to a majority of the footballing world, it does to two teams vying to claim ranks as the best English team in the game.
Second, Chelsea had won the League Cup earlier that year and United had won the league title a few weeks before. Both had been eliminated from the Champions League already and were only left with this one last title to play for. With trophies split evenly between them on the season, this match determined who would walk away with more silverware.
This was a match for bragging rights.
The two teams went a full 90 minutes without a goal. That does not mean there were not chances. Didier Drogba hit a free kick off the outside of the post. Ryan Giggs had a tap-in that he missed.
The breakthrough came with four minutes to go in extra time as Drogba scored his 33rd goal of the season with a brilliant one-two combination with Frank Lampard.
The goal gave them the win, the FA Cup and the title of being the first-ever cup winner in the new Wembley. It was only made sweeter by the fact that it was against United.
Manchester United 5-3 Chelsea (FA Cup: 04-01-1998)
5 of 11The 1996-97 season saw Chelsea win their first trophy in over 25 years as they took the FA Cup. Far from being the team they are now, the victory was hailed as a major accomplishment for a club on the rise.
However, luck would not favor them as they drew Manchester United in their first round.
United was looking for redemption from the previous season. The Red Devils went on to win the league in ’96-97 with relative ease, but Chelsea were a pain in their side as United were only able to take one point off them in their two meetings.
Once the whistle blew, Chelsea was in for one of their worst defeats at the hands of United in recent memory.
David Beckham got the scoring underway in the 23rd minute and followed it up in the 28th with another off one of his signature free kicks. Andrew Cole would add two more and Teddy Sheringham would wrap things up with another to make the score 5-0 with 25 minutes to go.
Chelsea scrapped back three goals of their own very late in the game, but the hole they dug was much too deep to ever consider getting out of.
It was a heartbreaking loss for the Blues that thought they could use the previous season’s momentum to escalate their game and win back-to-back silverware for the first time in the club's history. And while they would improve in the league itself, it was United who had the last laugh and let Chelsea know that they were still in charge.
Chelsea 3-0 Manchester United (Premiership: 29-04-2006)
6 of 11The Premier League race was not tight going into this match between the No. 1 and 2 teams in the league. Chelsea had the clear road to the trophy with 88 points, three games to go and United coming to Stamford Bridge. United had 79, making this the match for the title.
However, any faint hopes Sir Alex Ferguson had put in his players that they still had a chance to win the league were dashed almost the instant the two teams took the field.
William Gallas found the net in the fifth minute to give him his 12th and last goal in his Chelsea career and get the ball rolling for the Blues, as they would go on to win 3-0, the largest margin of victory for either side in their last 10 meetings.
The win was important for Chelsea because it clinched their second consecutive league title, establishing them as a force in England.
Many times teams will pop up, win a title out of nowhere and fade into nothing the following season; it happened to Chelsea in the 1955-56 season. After surprisingly winning their first league title the previous year, they would fall to 16th in the league (ironically enough, United won the title that season).
But two in a row cemented them as club that was on the verge of greatness. It was only made sweeter by the fact they were able to earn it in a resounding win against the Red Devils.
Chelsea 2-1 Manchester United (Premiership: 03-04-2010)
7 of 11Carlo Ancelotti’s first season in charge at the Bridge got off to the best of possible starts. Winning 12 of the first 14 games placed his side atop the table heading into the winter months. As usual, however, Chelsea stumbled in the cold and dropped to second behind United.
Even though the early April showdown between the two sides would not mathematically eliminate either of them, it was being penned as the match for the title. Both teams were playing excellent football as they had all season and the winner would be the leader of the league after the match and in control of their own fate.
In one of the most exciting games ever played between the two sides. Both had their chances to score, but it would be in the 20th minute when Joe Cole’s clever flick gave the Blues the lead.
The game continued as a close affair with United’s Dimitar Berbatov coming close on a number of occasions to evening the score.
Ancelotti made a move to bring on Didier Drogba in the 70th minute and less than 10 minutes later it would be rewarded when the Ivorian scored a controversial game-winner. The striker was clearly offside in video replay, but the linesman failed to see.
The win put Chelsea in the driver’s seat for the league and they did not look back, as they went on to return the title to Stamford Bridge for the first time in four years. A few weeks later they would win the FA Cup to give them their first double in the club's history.
Chelsea 1-0 Manchester United (Premiership: 15-07-2004)
8 of 11For the first time in the two clubs' history, Chelsea would meet United on Matchday 1. Both sides came into the season playing good ball the year before, but victims of Arsene Wenger’s Invincibles of Arsenal. With Jose Mourinho now firmly in charge at Stamford Bridge, the rivalry would reach new heights starting on this day.
Chelsea would score the only goal of the match, a header down from the newly acquired Didier Drogba to Eidur Gudjohnsen, who would put it away for the 1-0 win.
United fought all game, coming close on numerous occasions to tying up the affair, but were never quite able to do so.
The game itself marked the beginning of new era for the club. Mourinho gave five players (Petr Cech, Paulo Ferreira, Ricardo Carvalho, Alexeï Smertin and Didier Drogba) their debut in blue, with Cech and Drogba figuring prominently in the win.
But more importantly, it was the first game of a historic season for Chelsea. The team would finish with their best statistical record in the club's history (29-8-1) and give them their first league title in over 50 years.
The Chelsea we know today, the one competing at the top of Europe with the best in the world, began on this day and against Manchester United of all teams.
Manchester United 2-1 Chelsea (Premiership: 08-5-2011)
9 of 11Last season was one of the most emotionally difficult to watch as a Chelsea fan. The highs and lows were greater than ever, as Carlo Ancelotti’s side rushed out to one of the best starts in Premier League history only to come crashing down in the winter months. But in the end, it all came down to one game in May.
Chelsea had made a remarkable comeback and were now only three points back of first-place United with a win on this day putting them ahead on goal differential. The match at Old Trafford was all but mathematically for the title.
However, all the pregame pep and hype the club and fans had for this historic run came crashing down just 36 seconds in, as Javier Hernandez blew up the Theatre of Dreams with a goal. A mistake by newly acquired David Luiz allowed the Mexican behind the line to give United the early lead.
In the 23rd minute the stadium would erupt again as Nemanja Vidic put away a second. But the real man of the match was keeper Edwin van der Sar, who made a series of remarkable saves, ending his magnificent career on the best of terms.
The victory sealed United’s record 19th English league title, finally surpassing Liverpool and marking them the best English team of all time.
In regards to Chelsea, the match resonates more today than any other they have played. The loss sealed the fate of Carlo Ancelotti, and for better or worse gave us the team, the coach and the issues that are currently consuming the club.
Chelsea (5) 1-1 Manchester United (6) (Champions League Final: 21-05-2008)
10 of 11Arguably the most contentious match the two had ever played occurred in Moscow 2008. Owner Roman Abramovich’s long quest for European glory was finally within reach, in his native Russia of all places. Only United stood in their way.
With United already winning the league, Chelsea’s only hope of outshining the Red Devils was their first-ever Champions League title. The two sides split the season series at a win and loss apiece, with their second game coming to a head in some post-match tensions.
It all boiled over on a slippery surface in the Russian capital.
Cristiano Ronaldo, playing perhaps his best game ever in a big-time situation, put away a header 26 minutes in. Lampard responded just before the break with a goal of his own.
The game would continue with Chelsea taking the momentum from the end of the first half into the second as Didier Drogba burst out to force Edwin van der Sar into a good save and struck the woodwork with another.
In extra time, tensions started to flare as both teams felt the pressure of the moment. Drogba would be sent off for stupidly slapping Nemanja Vidic near the end of extra time. With the score 1-1 after 120 minutes of play, the title would be decided on penalties.
Both sides made their first two, but Chelsea got the advantage as Petr Cech read Ronaldo’s shot and pushed it away. Chelsea captain John Terry stepped up to take the kick with the score tied at four and only needing to make his to win the Champions League.
It was all set up for him: the storybook ending for the pride of Chelsea—the only player on the squad raised in the Chelsea academy and undeniably the face of the club. He could win it for his owner, his team and himself.
Instead, it turned into a nightmare that would haunt him forever. The poor surface that had been a concern all night gave way as Terry approached the spot, causing his plant foot to slip and the ball to sail over the net and into oblivion.
Three shooters later, van der Sar would block Nicolas Anelka’s penalty and give the win to United.
It was the biggest circumstances the two had ever met under and lived up to the billing. In my opinion, it was still one of the toughest games to watch as a Chelsea fan, but also one of the best sporting events I had ever seen.
Your Opinion?
11 of 11In the two clubs' 100-plus-year history they have met many more times than this. While the recent years have seen the matches escalate into a real rivalry, there are many in the past that have been just as important.
Making a list of 10 of the most defining is as subjective as it gets, so I encourage you to give your opinions. Which ones did I miss? Which matches do you remember?
Your opinion is as good as mine, so make it known!






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