Yes, once. Carlo Ancelotti won the 2009/10 Premier League with Chelsea in his first season in England, finishing on 86 points, one ahead of Manchester United.
When he won it and how the title was sealed
Ancelotti arrived at Chelsea in 2009 from AC Milan, and the title came in the first of his two seasons at the club. Chelsea secured it on the final day of the season with an 8-0 win over Wigan Athletic.
A key swing in the race came on 3 April 2010. Chelsea beat Manchester United 2-1 away, moved into the lead, and went into the final day with a one-point advantage.
The top four that season
Here are the top four finishers from that campaign.
| Position | Club | Points |
|---|---|---|
| 1 | Chelsea | 86 |
| 2 | Manchester United | 85 |
| 3 | Arsenal | 75 |
| 4 | Tottenham Hotspur | 70 |
That Chelsea title team's league records
Chelsea scored 103 league goals in the title season. According to the Premier League season review, they were the first top-flight team to reach a century of goals since Tottenham Hotspur in 1962/63.
Didier Drogba won the Golden Boot with 29 goals, while Frank Lampard recorded the most assists with 14.
Where Ancelotti sits among Premier League title-winning managers
Ancelotti is one of 13 managers to have won the Premier League. He is also one of four Italians on that list, alongside Antonio Conte, Claudio Ranieri and Roberto Mancini.
Chelsea and Manchester City have each won the Premier League under three different managers, more than any other club. Chelsea's three title-winning managers are Jose Mourinho, Ancelotti and Conte.
FAQ
Did Ancelotti win the Premier League with Chelsea?
Yes. His only Premier League title came with Chelsea.
It was won in 2009/10, his first season in England.
When did Ancelotti win the Premier League?
He won it in the 2009/10 season. The title was confirmed on the final day, when Chelsea beat Wigan Athletic 8-0.
How many Premier League titles does Ancelotti have?
He has one Premier League title. The Premier League's official list of title-winning managers includes him once.
Which Italian managers have won the Premier League?
Four Italians have won it: Ancelotti, Conte, Ranieri and Mancini. Ancelotti is one of that group.

