1999 or 2008 – What season was better for Man United?

For a club like Manchester United, just winning the Premier League isn’t enough to define it as one of their best seasons.

Winning the European Cup is essential for this.

In their 144 year history, United have won the European Cup three times.

The first came in 1968 under Sir Matt Busby’s reign, a decade after the tragedy in Munich. The second came in 1999, completing the famous treble, and the third in 2008 after beating Chelsea on penalties.

However, when seasons are evaluated, often the treble winners of 1999 are compared with the 2008 super squad.

But which was the better season?

Although it’s two trophies against three, the verdict isn’t so simple.

Premier League


By 1999, Sir Alex Ferguson had been managing United for 13 years. In this time, the Scot had already won the league four times, each coming after 1992’s inauguration of the Premier League.

However, the fabled European Cup had still defied him in this 13 year period.

Therefore, in 1998, Ferguson spent significantly in order to add the needed quality to take United that step further in Europe.

He brought in Italian winger Jesper Blomqvist, for seven million euros, 25 year old no nonsense defender Jaap Stam for 17m euros, and renowned goal scorer Andy Cole for 19.25m euros.

The year prior, United finished second in the Premier League with 77 points, just one point off Arsene Wenger’s Arsenal.

However, in the 1998/99 season, this flipped. Arsenal finished second on 78 points with Ferguson’s United one point ahead with 79. This secured United their first trophy of the three they earnt that year.


Nine years later, by 2008, Ferguson had won eight Premier League titles. Therefore, success in the league was no rare occurrence for the Manchester side.

However, by 2008, United were on a dry spell. The Red Devils had only won the league once since 2003.

The rivalry with Wenger’s Arsenal continued as the Gunners completed their invincible season, and the emergence of Jose Mourinho in 2004 with Chelsea, added to the difficulty of winning the league.

Having brought in future prospects like Wayne Rooney and Cristiano Ronaldo just years prior, Ferguson was rebuilding the United squad. Therefore, with additions like Michael Carrick in 2006, Nani, Owen Hargreaves and Carlos Tevez in 2007, this completed Ferguson’s desired rebuild.

Therefore, after winning the league in 2006/07, Ferguson hoped the gradual strengthening of the team would only bolster United’s chances of winning it again.

Ultimately, this was correct.

In 2007/08, United beat Chelsea to the title again. Despite the gap narrowing, Ferguson’s men did enough to win their 10th Premier League title.


In 2008, United won the league with 87 points, seven points more than in 1999.

Furthermore, it can be argued that the competitiveness of the league in 2008 with the rise of Chelsea under Mourinho and the continued strength of Arsenal was greater than that of 1999.

Consequently, in the Premier League, the 2008 season was more successful.

FA Cup


By 1999, United had won the FA cup three times under Ferguson’s regime. In 2023, the FA cups magnitude has faltered compared to its previous reputation.

However, back in 1999, it was a highly sort after trophy.

Therefore, Ferguson, unlike managers now, would not risk rotating too much, so to avoid an early exit.

In the third round, United beat Middlesborough 3-1 before edging past big rivals Liverpool 2-1 in the fourth round. After beating Fulham in the fifth round 1-0, United faced Chelsea. The initial fixture at Old Trafford wasn’t enough to separate the sides, and thus a 2-0 victory at Stamford Bridge was needed for Ferguson’s men to progress to the semi finals to face Arsenal.

This replayed semi final was one of the most iconic FA cup battles ever, subject to one of the greatest ever goals scored in it as well. Initially, a 0-0 draw at Villa Park saw the game replayed three days later.

In the replay, the scores were level in added time. Phil Neville gave away a penalty. Dennis Bergkamp stepped up, but Peter Schmeichel saved it. Then, in extra time, after a sloppy pass, Ryan Giggs drove at the Arsenal defence, passing four, before smashing it in to win United the game.

In the final, United beat Newcastle 2-0 at Wembley.


In the third round, United comfortably defeated Aston Villa 2-0.

Similarly, in the fourth round, United beat Tottenham Hotspur 3-1 at Old Trafford.

In the fifth round, United then destroyed Arsenal 4-0.

However, in the sixth round, Portsmouth ruined United’s treble chances.

After a bizarre game with Ferguson’s men unable to finish their chances, a late Portsmouth penalty saw the Pompey side knock United out of the cup.

Harry Redknapp’s Portsmouth then went onto win the competition. With Chelsea losing to Barnsley, this would have been the perfect opportunity for United to win the cup.


Therefore, in the FA cup, the 1999 team were far more successful as they managed to beat Liverpool, and a strong Arsenal side to win the cup. Whereas, in 2008, United faltered against Portsmouth.

Champions League


After being drawn into the group of death, United faced Bayern Munich, Barcelona and Brondby.

Despite playing against such tough opposition, the red devils avoided defeat beating Brondby twice and drawing the other games.

As a result, this meant United qualified in second, a point behind Bayern Munich in first.

In the quarter finals, United faced Inter Milan. The first leg saw a Dwight Yorke double seal victory. Subsequently a 1-1 draw in the second leg saw United through to the semi finals.

Similarly, Ferguson’s men were drawn against another Italian team in Juventus. This team featured the likes of Zinedine Zidane, Edgar Davids and Fillippo Inzaghi.

An injury time Ryan Giggs goal ensured United avoided defeat in a 1-1 draw at Old Trafford. In the second leg, Roy Keane picked up a booking which meant the captain was subsequently suspended for the final.

However, the Irishman produced a top quality selfless performance which saw him score and lead United to a 3-2 victory.

In the final, United faced Bayern Munich again. After an early lead, Bayern led for 90 minutes until two ‘Fergie time’ goals saw United steal the Champions League title away from the German side. This completed the treble making United the only English side to do so.


In 2008, United were handed an easier draw than that of 1999. They faced Roma, Sporting CP and Dynamo Kyiv.

Bar a 1-1 draw away to Roma, United won every game in the group. This comfortably placed them as group leaders, five points ahead of second.

In the first knockout round, United were drawn against Lyon. In France, United drew 1-1 thanks to a late Carlos Teves equaliser. However, at Old Trafford, a narrow 1-0 victory was enough to see United through.

In the Quarter final, United faced Roma again. Like in the group stage, Ferguson’s men were able to defeat Roma, this time home and away, safely sending United into the semi finals.

In the semi finals, United faced Barcelona. At the Camp Nou, nothing could separate the two sides after a 0-0 draw.

However, after another close game at Old Trafford, it was Paul Scholes thunderous volley which won United the game.

In the final, United faced Chelsea.

Cristiano Ronaldo opened the scoring before Frank Lampard levelled the game. After chances for both sides, the game went to extra time to decide a winner.

After extra time, the game was still deadlocked. Subsequently, it went to penalties.

John Terry had the chance to win Chelsea the cup but slipped.

Hereafter, Giggs scored his penalty, meaning Nicolas Anelka had to score. Anelka stepped up and Van der Sar saved it, securing United their third European Cup.


Although both sides won the Champions League, what sets them apart is the teams faced. In 1999, United avoided defeat throughout the competition, despite being drawn in the group of death, and then against huge teams like Inter and Juventus.

Whereas, although in 2008 United faced some tough sides in Barcelona and Chelsea, their run to the final was easier.

Thus, in the Champions League, the 1999 campaign was better than the 2007/08 season.

League Cup


After beating Bury 2-0 in the third round, and Nottingham Forest 2-1 in the fourth, United were knocked out in the fifth round by Tottenham Hotspur 3-1.


United were knocked out in the third round 2-0 by Coventry City.


Both sides failed to go far in the competition. Thus, it has little influence in the overall comparison.


Therefore, in the Premier League, the 2008 side had the better season.

However, in the Champions League and FA cup, the 1999 side were more successful, which gives them the edge.

Thus, the 1998/99 season was better than 2007/08 campaign.