October 3 1999: When Chelsea beat defending Premier League champions Manchester United 5-0

Chelsea and Manchester United are two teams that have become quite familiar with each other over the years. The London-based side became the main title opposition against the Red Devils in the mid-2000s. The Blues, transformed by the acquisition of Roman Abramovich, became a force to be reckoned with and often defeated Sir Alex Ferguson’s powerful side. That being said, it was not always like this. In the 1990s, Chelsea were a somewhat different side. They won the occasional domestic trophy but largely competed for top 4 league finishes. Which makes this match that we are about to discuss even more amazing.

The Blues completely thrashed the Red Devils at Stamford Bridge. Beating United was one thing: thrashing them 5–0 was quite another. Yet the latter is what happened on this very day in 1999.

After 22 years have passed, we look back at what was an unusual outcome at the time.


United were flying high in 1999 and came into the Chelsea game on top of the world. After all, it is worth remembering that this is the side that won the treble at the end of last year.

What’s more, he also had an unbeaten streak going on in the Premier League. Heading into the match at Stamford Bridge, they had not tasted defeat in 29 league games.

Chelsea, for their part, were seen as a side on the rise. Under the ownership of Ken Bates, they sought to add top-quality players and move up in the league.

The previous season had seen them finish third, and thus qualify for the Champions League for the first time. They also won the European Super Cup that year.

Thus, it was always going to be an extremely competitive match. It’s just that even the most optimistic of Chelsea fans could not have predicted what would happen.

Chelsea beat Manchester United 5–0

The opening strike for United was struck inside 30 seconds. Immediately after kick-off, Dan Petrescu sent a lobbed ball into the area.

It appeared, for all intents and purposes, to be a regulation ball tackle. But United goalkeeper Massimo Taibi made an absolute howler, colliding with Dennis Irvine as he went to collect.

This left an open net for any Chelsea player, and it was Gustavo Poyet who headed home. Understandably, the Stamford Bridge crowd went berserk.

The second one will not be long in coming. Another cross, this time from Albert Ferrer, saw Chris Sutton rise above and guide a well-hit looping header into the far corner.

However, the turning point of the match came from a clash between Dennis Wise and Nikki Butt. Chelsea captain Wise was always a feisty character and he got on the back of the butt in a 50-50 situation.

It was a poor challenge, but only a yellow card was eligible in those days. However, Butt had a brainfade for the ages when he decided to attack Wise after the challenge – right under referee Dermot Gallagher’s nose.

Butt was duly sent off and this led to a scuffle of sorts between the players. However, United now had the challenge of overturning a two-goal deficit with 10 men on the field.

The game-ending goal came in the 55th minute, when Poyet scored from the rebound after Taibi saved Frank Leboeuf’s shot.

And insult was added to injury when Henning Borg attempted to stop a Gianfranco Zola cross but only pushed the ball into his own net.

The final goal came 10 minutes from time, with Graeme Le Saux playing in Jody Morris. Morris coolly placed a shot past Taibi to cap off a five-star display.


From this point on, Chelsea and Manchester United would have very contrasting seasons. The Blues, under the management of Gianluca Vialli, would finish fifth in the league.

However, they would add another piece of silverware to their trophy cabinet by winning the FA Cup at the end of the season.

United would recover from this loss and go on to beat bitter rivals Leeds United for the Premier League title. They will also claim the Intercontinental Cup.

However, they did not defend their FA Cup title in order to participate in the FIFA Club World Cup – and also lost their Champions League crown when they were knocked out in the quarter-finals by Real Madrid.

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