Carlo Ancelotti is without doubt one of the greatest managers of all-time, having managed successful teams all over Europe to Champions League titles, domestic honours and international club winners’ medals – so his view on the game is taken as gospel by many across the world.
Ancelotti began his managerial career all the way back in 1995, having been Italy’s assistant manager at the 1994 World Cup, earning promotion to Serie A with Reggiana in the 1995-96 season. From there, he embarked on a managerial career that has seen him take control of the world’s best clubs, including Juventus, AC Milan, Chelsea, Bayern Munich, Paris Saint-Germain and two spells at Real Madrid.
Ancelotti Named Alex Ferguson as His Toughest Ever Opponent
The Man Utd legend continues to be one of the sport’s biggest-ever names
There aren’t many who have achieved more than him in the game, but one boss who could be in that conversation is Manchester United legend Sir Alex Ferguson – with current Brazil gaffer Ancelotti naming him as the toughest boss he ever faced.
|
Alex Ferguson’s record vs Carlo Ancelotti – record by competition |
||
|---|---|---|
|
Competition |
Games |
Wins-Draws-Losses |
|
Champions League |
8 |
4-1-3 |
|
Premier League |
4 |
1-0-3 |
|
Community Shield |
2 |
1-0-1 |
The two fared against each other 14 times, with the Italian slightly edging the battle with seven wins to Ferguson’s six – but that didn’t stop him from naming the Scot as his toughest-ever opposite number. He said, back in 2024:
“A lot of managers, but I have a good memory of Sir Alex [Ferguson] because we played a lot of times when I was here in Chelsea, in the Champions League when I was in Milan. I can say Sir Alex.
“I think he had the opportunity, because he did well to work a lot in the club and he was able to build a fantastic period in Manchester United.
“But of course, Alex Ferguson was a talented manager with a lot of ideas. He always had the respect of the opponents, and so I think he had an unbelievable career.”
Their first meeting came back in April 1999 in the Champions League semi-finals, as United drew with Juventus at Old Trafford – before a famous 3-2 win in Turin set them on their way to a famous treble, with a Roy Keane double putting the Bianconeri to the sword in one of the Champions League’s greatest-ever games.
But Ancelotti had the upper hand from there, winning six of their next seven head-to-heads – including winning both legs of a Champions League knockout clash with AC Milan in 2005 – before Ferguson finally got one over him in the Community Shield in 2010 when Ancelotti was Chelsea boss.
Ferguson then won their last three meetings, including a Champions League quarter-final win over the Blues in April 2011, before a 2-1 win at Old Trafford to all but win the Premier League with two games to spare just a month later.
Ancelotti has, of course, faced other bosses in his career, including Diego Simeone, Pep Guardiola, Roberto Mancini and more. But despite competing against Simeone twice as much with 28 games against, and Guardiola the same as Ferguson, it’s a nice tough to the United legend that Ancelotti has named him his toughest opponent in his three-decade-long career.
Statistics courtesy of Transfermarkt. Correct as of 25-06-25.
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