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Longest Serving Chelsea Managers of all-time

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longest serving chelsea managers under roman abramovich Antonio Conte
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Longest serving Chelsea managers of all-time!

Longest serving Chelsea managers of all-time? Which Chelsea managers have lasted the longest? Chelsea FC football managers? Jose Mourinho? Antonio Conte? Carlo Ancelotti? Who are The longest-lasting Chelsea managers? 

Here we look at the longest serving Chelsea managers of all-time. We will look throughout history of Chelsea FC past managers to find out who were the best.

When you think of long-serving Chelsea FC football managers, Jose Mourinho probably comes to mind (depending on your age). But you’ll be surprised to find out that Jose Mourinho doesn’t even reach the Top 5 longest serving Chelsea managers.

Being a manager is tough these days. The managerial turn-over is very high. Its not uncommon to see a manager get sacked after just a few bad results.

But back in the old days, Chelsea managers tended to last a lot longer. Perhaps it was a different time back then, or perhaps it’s because the current owner Roman Abramovich is very demanding. Expectations are higher for Chelsea managers these days and the stakes are high. Managers such as Jose Mourinho and Carlo Ancelotti have been sacked for one bad season. Those two are probably two of the top five managers in the world.

So we could safely say that managers back in the old days before Roman Abramovich took over lasted a lot longer. But, you can’t fault the Russian billionaire. Clearly it works. Chelsea have won dozens of top trophies since 2003. Before then, Chelsea hadn’t won the top league in 50 years!

Chelsea managers sacked Jose Mourinho Chelsea Managers list with most games managed Jose Mourinho

Longest serving Chelsea managers of all-time

So here we will list all Chelsea FC previous managers. In our Chelsea FC managers list, we will sort the managers from longest time at the club down to the shortest.

Longest serving all former Chelsea managers list

So finally, here are the longest-serving Chelsea managers of all-time.

Chelsea FC Manager From To Games
David Calderhead 01/08/07 08/05/33 966
Ted Drake 01/06/52 30/09/61 426
Dave Sexton 23/10/67 03/10/74 371
Tommy Docherty 01/10/61 06/10/67 303
Billy Birrell 19/04/39 31/05/52 293
Leslie Knighton 08/05/33 19/04/39 269
John Neal 28/05/81 11/06/85 203
Claudio Ranieri 17/09/00 31/05/04 199
José Mourinho 02/06/04 19/09/07 185
Bobby Campbell 06/03/88 12/05/91 165
Glenn Hoddle 04/06/93 10/05/96 157
John Hollins 11/06/85 06/03/88 145
Gianluca Vialli 12/02/98 12/09/00 143
José Mourinho 03/06/13 17/12/15 136
Carlo Ancelotti 01/06/09 22/05/11 109
Antonio Conte 03/07/16 25/06/18 106
Eddie McCreadie 16/04/75 01/07/77 97
Ian Porterfield 11/06/91 15/02/93 90
Ruud Gullit 10/05/96 12/02/98 83
Geoff Hurst 13/09/79 23/04/81 81
Ken Shellito 07/07/77 13/12/78 66
Avram Grant 20/09/07 24/05/08 54
John Tait Robertson 01/08/05 27/11/06 54
Rafael Benítez 21/11/12 27/05/13 48
Maurizio Sarri 30/06/2018 Present 45
Roberto Di Matteo 04/03/12 21/11/12 42
André Villas-Boas 22/06/11 04/03/12 40
Luiz Felipe Scolari 01/07/08 09/02/09 36
Ron Suart 03/10/74 16/04/75 34
Danny Blanchflower 14/12/78 11/09/79 32
Guus Hiddink 19/12/15 16/05/16 27
William Lewis 27/11/06 01/08/07 27
Guus Hiddink 16/02/09 30/05/09 22
David Webb 15/02/93 11/05/93 13
Bobby Gould 23/04/81 01/05/81 2
Graham Rix
Ray Wilkins
13/09/00 17/09/00 2
Ron Suart 06/10/67 23/10/67 2
Ray Wilkins 09/02/09 15/02/09 1
Steve Holland 17/12/15 19/12/15 1

Number one longest-serving Chelsea manager of all-time: David Calderhead

David Calderhead is the longest serving Chelsea manager ever. The Scotsman was in charge of Chelsea from 1907 to 1933! That’s 26 years. That’s 966 games!

Calderhead was the first ever manager at Chelsea. Despite competing in a few cup finals, he never managed to win any silverware. Sadly, Calderhead died five years after he left Chelsea at the age of 73.

Second longest-serving Chelsea manager of all-time: Ted Drake

Longest serving Chelsea managers of all-time Ted Drake

Ted Drake was the second longest-serving Chelsea manager. The Englishman was in charge at Chelsea from 1952 to 1961. Drake managed 426 games. He won 156 of them with a win percentage of 37%.

Third longest serving Chelsea manager: Dave Sexton

Dave Sexton Top Longest serving Chelsea managers of all-time

Dave Sexton is the third longest-serving manager of all-time. Sexton managed Chelsea from 1967 to 1974. That’s 371 games as manager of Chelsea.

Chelsea FC former managers that won titles list.

All ex Chelsea managers with honours list. All the Chelsea managers that have won titles list. This includes Chelsea managers since 2000.

Previous Chelsea Managers with honours list

Name Nat Tenure Honours
Ted Drake  England 1952–1961 1955 First Division
1955 FA Charity Shield
Tommy Docherty  Scotland 1961–1967 1965 Football League Cup
Dave Sexton  England 1967–1974 1970 FA Cup
1971 European Cup Winners’ Cup
John Neal  England 1981–1985 1984 Second Division
John Hollins  England 1985–1988 1986 Full Members Cup
Bobby Campbell  England 1988–1991 1989 Second Division
1990 Full Members Cup
Ruud Gullit  Netherlands 1996–1998 1997 FA Cup
Gianluca Vialli  Italy 1998–2000 1998 Football League Cup
1998 UEFA Cup Winners’ Cup
1998 UEFA Super Cup
2000 FA Cup
2000 FA Charity Shield
José Mourinho  Portugal 2004–2007
2013–2015
2005 Football League Cup
2005 Premier League
2005 FA Community Shield
2006 Premier League
2007 Football League Cup
2007 FA Cup
2015 Football League Cup
2015 Premier League
Guus Hiddink  Netherlands 2009
2015–2016
2009 FA Cup
Carlo Ancelotti  Italy 2009–2011 2009 FA Community Shield
2010 Premier League
2010 FA Cup
Roberto Di Matteo  Italy 2012 2012 FA Cup
2012 UEFA Champions League
Rafael Benítez  Spain 2012–2013 2013 UEFA Europa League
Antonio Conte  Italy 2016–208 2017 Premier League

2018 FA Cup

See also: 

Top five most wins by a Chelsea manager – Win %

Best Chelsea managers ever

Chelsea FC Managers

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