Chelsea's 5 best managers of the modern era

Choosing the best managers in Chelsea’s modern era is a fight between the head and the heart. I have judged them on three things: the trophies they won, the games that defined them, and the mark they left on the club. Results that can be checked count for more than feelings, though I admit the feelings crept in.

One of the five won nothing at Chelsea and still makes the list. That tells you how I weigh impact. We count down from five.

5. Claudio Ranieri

Ranieri has no trophy to his name at Chelsea, so this is a ranking on the work he did before the trophies came. In 2003-04 we finished second in the Premier League, behind an unbeaten Arsenal side. It was our highest league finish in half a century.

That season also took us to the Champions League semi-finals. Monaco ended it, winning 5-3 on aggregate. We lost the first leg 3-1 away and drew the second 2-2 at home. It was painful, but it showed this club belonged at the top table.

Ranieri was sacked after four years in charge, and Jose Mourinho replaced him. Chelsea’s modern story needed a springboard, and he built one. For a deeper look at how the managerial merry-go-round turned, see our piece on all Chelsea managers and trophies under Abramovich.

4. Antonio Conte

Conte won the Premier League in his first season in charge, 2016-17, and he did it in style. We finished on 93 points, seven clear of second-placed Tottenham. We won 30, drew 3 and lost 5 of our 38 league matches, and the Premier League’s own site describes those 30 wins as a record. We clinched the title with a 1-0 win at West Bromwich Albion.

He was named Barclays Manager of the Season, only the third manager to win the award in a debut Premier League campaign. It was a deserved honour, and the club had held talks with him while he was Italy boss to land him.

The ending was messier. We lost the 2017 FA Cup final 2-1 to Arsenal on 27 May, and Conte was sacked on 12 July 2018. The title keeps him in fourth, and the 2016-17 team was a joy. You can see how he spoke about his future afterwards in Antonio Conte Talks About a Future in Italy.

3. Carlo Ancelotti

Ancelotti’s first season, 2009-10, delivered the Premier League and FA Cup double. It was a calm, assured piece of management from a man who made winning look easy.

The football was gloriously direct too. We scored 103 league goals that season, the first century by a top-flight team since Spurs in 1962/63. Those goals were what made the title feel like a statement and not just a trophy.

I put him third because the success was concentrated in one remarkable season. Even so, it is one of the best any Chelsea manager has produced. He is also a manager whose standing sometimes gets overlooked, a theme we touched on in Deeplinks: Ancelotti the Forgotten Man.

2. Roberto Di Matteo

Di Matteo takes second place for one night in Munich. He took over as interim manager after Andre Villas-Boas was sacked in March 2012, and within weeks he had the club on a road nobody expected.

On Saturday 19 May 2012 at the Allianz Arena, we drew 1-1 with Bayern Munich after extra time and won 4-3 on penalties. Didier Drogba had equalised in stoppage time, and Arjen Robben missed an extra-time penalty. Then Drogba scored the decisive spot-kick. Chelsea became the first London club to win the Champions League.

That was not all. On 5 May 2012 we beat Liverpool 2-1 at Wembley in the FA Cup final, his first trophy as a manager. He had also scored in Chelsea’s FA Cup run as a player, so it felt like a circle closing. He was given a two-year deal that June and dismissed in November 2012. It was a short reign, but he did what no one before him had done. I will take that every time.

1. Jose Mourinho

There was never any real argument. Mourinho arrived in June 2004 and changed what Chelsea were. In his first spell he led us to two Premier League titles (2004-05 and 2005-06), two League Cups (2004-05 and 2006-07) and an FA Cup (2006-07).

The 2004-05 title was our first top-flight title in 50 years. After that double of the League Cup and the Premier League, he earned a new contract in 2005. The mentality he built, where we expected to win and usually did, is what the club has lived on since.

He came back for a second spell from 2013 to 2015 and added another Premier League title and another League Cup. Look back at 30 Stats from Chelsea’s 2014-15 Title-Winning Season to see how complete that team was. Five trophies in the first spell, two more in the second, and a standard that all of his successors are measured against. He is first on trophies, first on impact, and first in the hearts of plenty of us.

The verdict

Mourinho set the bar, Di Matteo gave us a night we will never forget, Ancelotti and Conte each delivered title-winning teams, and Ranieri laid the foundations. Whoever is in the dugout now has some serious company to live up to. If you want to see the players who played for these managers, read our lists of Chelsea’s 5 best midfielders since 2000 and Chelsea’s 5 best goalkeepers of all time.