Best and Worst Matches in Manchester United History

There have been some real Glory Nights at Old Trafford – games that will live long in the memory of all supporters as they become part of the club’s folklore. Amongst all the success, there have been some downsides too, although, happily, they are much rarer.

So, what are the best and worst games in Manchester United’s history? Here is a rundown.

Best Games in Manchester United’s History

1999 – Champions League Final: Bayern Munich 1 vs Manchester United 2

Could this be the greatest game of all time, let alone Manchester United’s best? It would certainly be tough to equal this in terms of drama as two injury time goals swung the match United’s way after Bayern had led from the sixth minute.

Mario Basler had opened the scoring for the German side early on, and although there were chances at either end, it seemed certain that Bayern Munich would coast to the win. All that changed after 90 minutes as Teddy Sheringham levelled things up before Ole Gunnar Solskjaer’s unforgettable winner, deep into stoppage time.

1968 – European Cup Final: Benfica 1 vs Manchester United 4

More than 30 years earlier, United had claimed their first European title with a win at Wembley over Portuguese Champions Benfica. For manager Matt Busby, it was an emotional evening, ten years on from the Munich air disaster that had claimed the lives of so many great players.

The game itself was far more comfortable than the 1999 final, even though the match was at 1-1 after 90 minutes. Three extra time goals sealed the victory with Bobby Charlton (2), George Best and Brian Kidd the men on the scoresheet.

1995 – Premier League: Manchester United 9 vs Ipswich Town 0

United’s record league win is a 10-1 victory that they achieved against Wolves way back in 1892 but in the modern era, this result against Ipswich was really quite staggering. It also set an individual Premier League record – which has since been equalled – as Andy Cole scored five of those nine goals.

Other goals came from Mark Hughes (2), Roy Keane and Paul Ince, and this remains a record winning margin in Premier League history. Ipswich were relegated at the end of the season, and while that underlines the relative strengths of the two teams, it remains an incredible achievement.

FA Cup Semi Final Replay 1999: Manchester United 2 vs Arsenal 1

This semi final replay at Villa Park will always be remembered for Ryan Giggs’ stunning winning goal in extra time, and it’s easy to forget just how much drama this game actually held. United had taken a 17th minute lead through David Beckham before Dennis Bergkamp equalised in the second period.

Meanwhile, United had lost their skipper Roy Keane who was sent off for two bookable offences and they needed a last minute penalty save from Peter Schmeichel to keep them alive.

It all led up to Giggs’ moment as he took the ball on the half way line before dribbling through five defenders and blasting past David Seaman into the roof of the net. Manchester United went on to complete the historic treble that year, courtesy of that Champions League victory over Bayern Munich and a rather more comfortable, 2-0 win over Newcastle United in the FA Cup Final at Wembley.

2011 – Premier League: Manchester United vs 8 Arsenal 2

The 9-0 victory over Ipswich Town may have set a number of records, but when you put this game into context, the 8-2 demolition of Arsenal was far more impressive. Arsenal were a much stronger team, and while they may have been fading at the end of the Arsene Wenger reign, they were a tougher side to crack at the start of the 2011-12 season.

United simply took them apart with Wayne Rooney, at the peak of his powers, scoring a hat trick while Ashley Young (2), Danny Welbeck, Nani and Ji-Sung Park also got in on the act. The Red Devils were 3-1 up at half time, but nothing could have prepared fans for the second half deluge.

Arsenal’s late second rally proved to be scant consolation but the scorer, Robin Van Persie, may have decided there and then that his future lay away from the Emirates as he joined Manchester United at the end of the same season.

Worst Matches in Manchester United’s History

2011 Premier League: Manchester United 1 vs Manchester City 6

United have lost by a five goal margin on three separate occasions in the Premier League, but this is the result that would have hurt the most. Not only did the reverse take place on their own Old Trafford ground, it came against bitter rivals Manchester City.

It’s true that City were enjoying the fortunes that their new owners had bestowed upon them but the margin of defeat was still amazing. Only a solitary Darren Fletcher goal in the 81st minute provided any consolation from what was a miserable day.

2023 – Premier League: Liverpool 7 vs Manchester United 0

While the 2022/23 season was a positive one for Manchester United as a whole, this was the lowest point of the campaign by some distance. It was also United’s heaviest Premier League defeat, and their joint biggest loss of their entire history.

Liverpool were rampant in the second period after a subdued first half. The Reds only took the lead in the 43rd minute through Cody Gakpo, before Manchester United capitulated. Gakpo scored again, while Mohamed Salah and Darwin Nunez also scored twice. Substitute Roberto Firmino, completed the 7-0 win late on, but United fans had left long before that point.

1974 – First Division: Manchester United 0 Manchester City 1

The Manchester United team of the mid-70s was a far cry from the side that had lifted the European Cup just a few years earlier. With Bobby Charlton and George Best coming to the end of their United careers, the club couldn’t adequately replace them, and by the end of the 1973/74 campaign, they were relegated to the old second division.

It’s often wrongly claimed that Denis Law’s goal for City in the Manchester derby sealed their relegation, and the result effectively meant that it was all over. In fairness it was a great goal – a classy back heel beyond Alex Stepney – but Law was visibly upset that his effort had ended hopes of survival for his former team.

Good or bad, we will always follow United but these games, more than most, will linger long in our collective memories.