Arsenal vs Manchester United in 1999: What if Dennis Bergkamp scored that penalty in FA Cup semi-final replay?

Arsenal vs Manchester United in 1999: What if Dennis Bergkamp scored that penalty in FA Cup semi-final replay? looks at key moments in football history, where events could so easily have taken a different course and asks, what if?

It has been 20 years since Arsenal and Manchester United‘s thrilling FA Cup match. It was a game that had everything from red cards, glorious goals and here, ponders what if Dennis Bergkamp scored THAT penalty in the dying moments?

What happened?

United and Arsenal were battling on all fronts domestically in the 1998/99 season. The former were on the verge of sealing the treble, but the latter were looking to win a second successive League and Cup double.

The rivals, and hands down the two best teams in the land, were evenly matched throughout the campaign, but in the end United pipped the Gunners to the Premier League crown by a point on the final day of the season and dumped them out of the FA Cup in the semi-final in the process.

That league campaign was breathtaking and is perhaps forgotten about due to Man United’s clean sweep on the trophy front.

Arsenal, with Patrick Vieira, Tony Adams, Nicolas Anelka and Bergkamp were a well-balanced side blessed with flair, toughness and a very mean defence. Between January and May the back four conceded just six goals.

Only one team could halt their quest for total domination again and in the semi-final replay at Villa Park on 14 April, Arsenal were beaten in extra-time thanks to a memorable Ryan Giggs goal.

But before that there were 90 minutes of pure drama.

David Beckham and Bergkamp scored two great goals, Roy Keane was sent off with around 15 minutes remaining and, as full-time edged closer and people anxiously checked their watches, Ray Parlour was brought down by an exhausted Phil Neville in the 18-yard box.

Penalty to Arsenal.

“I would have had my house on Dennis Bergkamp scoring the penalty,” Parlour later said.

“I remember asking the referee David Elleray how long was left and he said, ‘This is the last kick of the game’. It was Dennis versus Schmeichel and he saved it.”

Cue euphoria from United.

Schmeichel celebrating Manchester United’s win at Villa Park in 1999

But what if he didn’t miss?

Well, Giggs would not have scored his wonder goal and Arsenal would have contested the FA Cup final against Newcastle instead. United’s treble dream would have been over, much to the delight of Liverpool fans; the Reds having celebrated their own treble success – First Division, European Cup and League Cup – 15 years earlier.

It was neck-and-neck in the title race at the time – a point separated them – and a win could well have provided Arsenal with the boost needed to win the league instead.