Chelsea's 12 best managers of all time
Jose Mourinho, 2004-07 & 2013-15
A master man manager and tactician who was occasionally a victim of his own volatility.
Arrived at the Bridge from Porto as the self-styled ‘Special One’ and quickly went about proved it, winning the Premier League title with a record points total of 95 and – despite having a reputation as a defensive/counter-attacking coach – in some style too, playing with two out-and-out wingers in Arjen Robben and Damien Duff.
Always fell short in Europe, unlike at Porto and Inter, but added another Premier League title, two League Cups and an FA Cup in his first spell, then returned in 2013 to claim another Premier League title. A master man-manager and tactician who was occasionally a victim of his own volatility.
Ted Drake, 1952-61
A fine centre-forward for Arsenal and England in the 1930s, Drake made sweeping changes at Stamford Bridge, removing the Pensioners from the club’s nickname and logo, putting more emphasis on ball work in training and eschewing big-name signings in favour of scouring the lower leagues for untapped talent. The results were spectacular.
Within three years, Chelsea had won their first-ever league title, Drake becoming the first to do so as player and manager. Though further silverware eluded him, he later brought through a talented crop of youngsters including Bobby Tambling and Jimmy Greaves.
Dave Sexton, 1967-74
The Londoner was a coach first, manager second, studying teams abroad and encouraging a passing game based on tactical discipline and interchanging of positions.
Took ‘Docherty’s Diamonds’ (see below) and polished them into a cult team, winning the FA Cup and European Cup Winners’ Cup with the likes of Peter Osgood, Peter Bonetti, Alan Hudson and Ron ‘Chopper’ Harris.
The Londoner was a coach first, manager second, studying teams abroad and encouraging a passing game based on tactical discipline and interchanging of positions. On the downside, he struggled to control the team’s King’s Road set, which eventually prompted his departure.
Carlo Ancelotti, 2009-11
Deserved better that being sacked just hours after Chelsea’s final league game of the season.
A more progressive coach than many of his countrymen, the amiable Italian arrived with a big reputation and left with it intact courtesy of Premier League and FA Cup wins in his first season.
Like many in the Abramovich era he then paid for one below-par campign as the Blues came in well behind Manchester United in the league and came up short in the Champions League – a title Ancelotti was expected to deliver. He’d done it before, he’s done it since, and given a little time, who knows? Deserved better that being sacked just hours after Chelsea’s final league game of the season.
Glenn Hoddle, 1993-96
Hoddle arrived as player-manager at the Bridge off the back of working miracles with Swindon
A better coach than psychologist, Hoddle arrived as player-manager at the Bridge off the back of working miracles with Swindon. He left to coach England, having made the Blues easy on the eye, competitive in the cups and – with Hoddle’s reputation as a player, particularly with Monaco – attractive to foreigners looking for a move to the fledgling Premier League.
None more so than Ruud Gullit, arguably the most important signing in the club’s history.
Roberto Di Matteo, 2012
There has to be a place for Chelsea’s only Champions League-winning coach, even if he did inherit the spine of a team built by Mourinho.
Having scored two FA Cup final winners as a midfielder for the Blues, the Italian was already in credit when, following promising spells in charge of MK Dons and West Brom, he succeeded Andre Villas-Boas, who had hired Di Matteo has his assistant.
The caretaker more than steadied the ship, though, winning the FA Cup as well as Old Big Ears, as Chelsea – without the suspended John Terry – memorably beat Bayern Munich on penalties after the Germans dominated a 1-1 draw. The bar had been set high – too high, in fact.
Having been handed a two-year contract in June, Di Matteo was out of a job by November, sacked with Chelsea on the verge of Champions League elimination. Harsh.
- ONE-ON-ONE Roberto Matteo's career reflection