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Most Memorable Managers In Chelsea F.C. History featuring David Calderhead

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guus hiddink

Founded over 100 years ago, Chelsea F.C. has been through 29 permanent and 6 interim managers since its formation, with each one leaving a legacy different to the other – for better or for worse. But which of these have been particularly influential for the club? Here is a list of five of the most memorable that long-standing fans, and new ones alike, might recognise.

David Calderhead

The oldest icon on our list, Calderhead was Chelsea’s first manager (while also serving as joint secretary) for almost 26 years. He stayed with the team from their initial foundation in 1907 through to 1933 and sadly died five years later. He was born in 1864 and played for Queen of the South Wanderers, Notts County and Lincoln City during his time as a professional footballer. His biggest achievement was getting Chelsea into the 1915 FA Cup finals, which they lost to Sheffield United. 

Another interesting fact was that Calderhead was incredibly quiet in the media of Chelsea club news. This earned him the nickname of ‘The Sphinx of Stamford Bridge’, hence not much publicly accessible information is available about him today.

Today, many football fans across the country bet on Chelsea in the Premier League to back their favourite players and more, along with betting on other tournaments such as the World Cup at sites like

Jose Mourhino

Jose Mourinho,Frank Lampard & John Terry Chelsea Champions 2004-2005 Chelsea V Charlton Stamford Bridge, Chelsea London, England 07 May 2005 PUBLICATIONxINxGERxSUIxAUTxONLY Copyright: Allstar/RichardxSelle 12820085

Nicknamed ‘The Special One’ after a press conference covered by the media, Jose Mourhino was born in Portugal to a large middle-class family, where an uneventful career as a midfielder led him into managing. The current head coach of Associazione Sportiva Roma, Mourhino is widely regarded as being one of the best managers of all time, and his service to Chelsea has never gone unnoticed. 

In 2004, he was contracted to Chelsea for three years, in which he won the 2005 FA Community Shield, the Premier League in 2005 and 2006 consecutively, and the Football League Cup in both 2005 and 2007. He had an impressive win percentage of 67%.

It is no surprise that he was hired again in 2013, though he was unfortunately sacked during the 2015 season to make way for Guus Hiddink.

Guus Hiddink

guus hiddink
guus hiddink

This former manager has the highest percentage of wins out of any other. He was born in Varsseveld, a town in the Netherlands, during the autumn of 1946, and would later become a professional midfielder. After his retirement in 1982, he began one of the most successful careers in football team management, with his first being the native Philips Sport Vereniging. After Luiz Felipe Scolari was sacked in February 2009, Chelsea hired Guus Hiddink to take charge of the team until the end of the season. 

Despite being the manager for a few months, he had a phenomenal win rate of 73% due to only losing 1 game out of the 22 he oversaw. When Hiddink returned as a caretaker manager from 2015 to 2016, he managed to achieve a win rate of 58%, despite it being a terrible season following the sacking of Jose Mourhino.

Carlo Ancelotti

Carlo Ancelotti (Photo by OLI SCARFF/AFP via Getty Images)

Born in June 1956, this Italian manager and former player was in charge of Chelsea from 2009 to 2011 after taking over from Hiddink. He had plenty of achievements, including a record-breaking 67 victories and the third-best win percentage in the Premier League’s history – a statistic that lived up to his name until 2016. He was dismissed after a defeat at Everton on the 22nd of May but is still widely regarded as one of the best managers to date.

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