Chelsea’s most successful period has coincided with the arrival of Roman Abramovich and his billions, but there were successful managers at Stamford Bridge before he was. Here we look at the top five Chelsea managers of all time.
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Gianluca Vialli
Vialli took over from Gullit and made what was a good team pre-Abramovich even better. The calibre of Chelsea’s foreign signings improved under the Italian and he turned them from a mid-table side into a consistent top-flight force. The third place finish he achieved in 1999 was the club’s highest since 1970, leading the Blues to a first-ever Champions League appearance which featured a 3-1 win over Barcelona.
Trophies: FA Cup 1999/2000, League Cup 1997/98, Charity Shield 2000, UEFA Cup Winners’ Cup 1997/98, UEFA Super Cup 1998
Games Managed: 143
Time in Charge: 1998-2000
Memorable Achievement: Guiding Chelsea to a 3-1 victory over Barcelona in the Champions League.
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Roberto Di Matteo
The former Chelsea midfielder was initially appointed as caretaker manager, replacing Andre Villas-Boas midway through the 2011/12 season. Chelsea had been struggling throughout the campaign, but under Di Matteo, they won the FA Cup and more impressively, went on to win the Champions League without a suspended John Terry. He was handed the role on a permanent basis, but he’d set the bar too high and was sacked by November of the following season.
Trophies: FA Cup 2011/12, Champions League 2011/12
Games Managed: 42
Time in Charge: 2012
Memorable Achievement: Being the only Chelsea manager to win a Champions League.
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Carlo Ancelotti
Ancelotti arrived with a big reputation and lived up to it in his first season, winning both the Premier League and FA Cup double. But like many managers under Abramovich, the following year wasn’t as good and he was relieved of his duties, just hours after Chelsea’s final league game of the season.
Trophies: Premier League 2009/10, FA Cup 2009/10, Community Shield 2009
Games Managed: 109
Fan Approval: Fans loved him as he won games playing in an entertaining style of football
Time in Charge: 2009-11
Memorable Achievement: His first season as manager was Chelsea’s first double-winning season.
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Ted Drake
A former Arsenal and England striker of the 1930s, Drake made many changes at Stamford Bridge, removing the Pensioners from the club’s nickname and logo and favouring big-name signings instead of scouting the lower leagues. Within three years of his arrival, Drake lead Chelsea to their first and only league title of the 20th century and although he didn’t win anything else as manager, he nurtured youngsters Bobby Tambling and Jimmy Greaves who went on to become legends.
Trophies: First Division 1954/55
Games Managed: 425
Time in Charge: 1952-61
Memorable Achievement: Revolutionised Chelsea, introducing the “Lion Rampant Regardant” crest and the Blues nickname.
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Jose Mourinho
He proclaimed himself as the “Special One” in his first press conference and proved it by winning the Premier League with a record points total of 95. He retained his title, but a disagreement with Roman Abramovich saw him depart in 2007. He returned for a second spell in 2013, winning another league title, but a disappointing start to a title defence was combined with fall-outs between him and players, physios and fans, leading to him to depart Stamford Bridge for a second and likely final time as Chelsea manager.
Trophies: Premier League (2004/05, 2005/06, 2014/15), FA Cup 2006/07, League Cup (2004/05, 2006/07, 2014/15), Community Shield 2005
Games Managed: 321
Time in Charge: 2004-2007 and 2013-2015
Memorable Achievement: He’s Chelsea’s most successful manager of all-time, leading them to three Premier League triumphs.
