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Longest Serving Chelsea Managers of all-time

May 22, 2024

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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. Watch & Bet Football Here =>

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!

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. Watch & Bet Football Here =>

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
Thomas Tuchel	26/01/21	07/09/22	100
Eddie McCreadie	16/04/75	01/07/77	97
Frank Lampard	16/06/19	25/01/21	95
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
Maurizio Sarri	30/06/2018	16/06/2019	63
Avram Grant	20/09/07	24/05/08	54
John Tait Robertson	01/08/05	27/11/06	54
Mauricio Pochettino	01/07/23	21/05/24	51
Rafael Benítez	21/11/12	27/05/13	48
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
Graham Potter	08/09/22	02/04/23	31
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
Bruno Saltor	02/04/23	06/04/23	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. Watch & Bet Football Here =>

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