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Chelsea: The Premier League Years

Can you name all of Chelsea's managers and captains during the PL era, as well as their top appearance makers, top scorers, most expensive purchases and most expensive sales per season?
Excludes caretaker managers
Check out the full Premier League Years series!
Quiz by
JustJoshing
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Last updated: May 27, 2025
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First submittedDecember 9, 2016
Times taken1,368
Average score51.4%
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1992/93
Manager
Ian Porterfield
David Webb
Captain
Dennis Wise
Most Appearances
Andy Townsend
Top Scorer
Mick Harford
Player of the Year
Frank Sinclair
 
 
1995/96
Manager
Glenn Hoddle
Captain
Dennis Wise
Most Appearances
Dennis Wise
Top Scorer
John Spencer
Player of the Year
Ruud Gullit
 
 
 
 
1998/99
Manager
Gianluca Vialli
Captain
Dennis Wise
Most Appearances
Ed de Goey
Gianfranco Zola
Top Scorer
Gianfranco Zola
Player of the Year
Gianfranco Zola
 
 
2001/02
Manager
Claudio Ranieri
Captain
Marcel Desailly
Most Appearances
Frank Lampard
Top Scorer
Jimmy Floyd Hasselbaink
Player of the Year
Carlo Cudicini
 
 
 
 
2004/05
Manager
José Mourinho
Captain
John Terry
Most Appearances
Frank Lampard
Top Scorer
Frank Lampard
Player of the Year
Frank Lampard
 
 
 
 
2007/08
Manager
José Mourinho
Avram Grant
Captain
John Terry
Most Appearances
Joe Cole
Top Scorer
Frank Lampard
Player of the Year
Joe Cole
 
 
2010/11
Manager
Carlo Ancelotti
Captain
John Terry
Most Appearances
Petr Čech
Florent Malouda
Top Scorer
Nicolas Anelka
Player of the Year
Petr Čech
 
 
 
 
 
 
2013/14
Manager
José Mourinho
Captain
John Terry
Most Appearances
Branislav Ivanović
Top Scorer
Eden Hazard
Player of the Year
Eden Hazard
 
 
 
 
 
 
2016/17
Manager
Antonio Conte
Captain
John Terry
Most Appearances
César Azpilicueta
Top Scorer
Diego Costa
Player of the Year
Eden Hazard
 
 
2019/20
Manager
Frank Lampard
Captain
César Azpilicueta
Most Appearances
Mason Mount
Top Scorer
Tammy Abraham
Player of the Year
Mateo Kovačić
 
 
 
 
 
 
2022/23
Manager
Thomas Tuchel
Graham Potter
Frank Lampard
Captain
César Azpilicueta
Most Appearances
Conor Gallagher
Kai Havertz
Top Scorer
Kai Havertz
Player of the Year
Thiago Silva
1993/94
Manager
Glenn Hoddle
Captain
Dennis Wise
Most Appearances
Dmitri Kharine
Top Scorer
Gavin Peacock
Mark Stein
Player of the Year
Steve Clarke
 
 
1996/97
Manager
Ruud Gullit
Captain
Dennis Wise
Most Appearances
Roberto Di Matteo
Mark Hughes
Top Scorer
Mark Hughes
Player of the Year
Mark Hughes
 
 
1999/00
Manager
Gianluca Vialli
Captain
Dennis Wise
Most Appearances
Ed de Goey
Top Scorer
Tore André Flo
Player of the Year
Dennis Wise
 
 
 
 
2002/03
Manager
Claudio Ranieri
Captain
Marcel Desailly
Most Appearances
Frank Lampard
William Gallas
Top Scorer
Gianfranco Zola
Player of the Year
Gianfranco Zola
 
 
2005/06
Manager
José Mourinho
Captain
John Terry
Most Appearances
Frank Lampard
John Terry
Top Scorer
Frank Lampard
Player of the Year
John Terry
 
 
2008/09
Manager
Luiz Felipe Scolari
Guus Hiddink
Captain
John Terry
Most Appearances
Frank Lampard
Top Scorer
Nicolas Anelka
Player of the Year
Frank Lampard
 
 
2011/12
Manager
André Villas-Boas
Roberto Di Matteo
Captain
John Terry
Most Appearances
Petr Čech
Top Scorer
Frank Lampard
Player of the Year
Juan Mata
 
 
 
 
 
 
2014/15
Manager
José Mourinho
Captain
John Terry
Most Appearances
Eden Hazard
Top Scorer
Diego Costa
Player of the Year
Eden Hazard
 
 
 
 
 
 
2017/18
Manager
Antonio Conte
Captain
Gary Cahill
Most Appearances
Willian
Top Scorer
Eden Hazard
Player of the Year
N'Golo Kanté
 
 
2020/21
Manager
Frank Lampard
Thomas Tuchel
Captain
César Azpilicueta
Most Appearances
Mason Mount
Top Scorer
Tammy Abraham
Timo Werner
Player of the Year
Mason Mount
 
 
2023/24
Manager
Mauricio Pochettino
Captain
Reece James
Most Appearances
Conor Gallagher
Top Scorer
Cole Palmer
Player of the Year
Cole Palmer
1994/95
Manager
Glenn Hoddle
Captain
Dennis Wise
Most Appearances
Gavin Peacock
Top Scorer
Paul Furlong
John Spencer
Player of the Year
Erland Johnsen
 
 
1997/98
Manager
Ruud Gullit
Gianluca Vialli
Captain
Dennis Wise
Most Appearances
Frank Lebœuf
Top Scorer
Gianluca Vialli
Player of the Year
Dennis Wise
 
 
2000/01
Manager
Gianluca Vialli
Claudio Ranieri
Captain
Marcel Desailly
Most Appearances
Gianfranco Zola
Top Scorer
Jimmy Floyd Hasselbaink
Player of the Year
John Terry
 
 
2003/04
Manager
Claudio Ranieri
Captain
Marcel Desailly
Most Appearances
Frank Lampard
Top Scorer
Jimmy Floyd Hasselbaink
Player of the Year
Frank Lampard
 
 
 
 
2006/07
Manager
José Mourinho
Captain
John Terry
Most Appearances
Frank Lampard
Top Scorer
Didier Drogba
Player of the Year
Michael Essien
 
 
 
 
2009/10
Manager
Carlo Ancelotti
Captain
John Terry
Most Appearances
John Terry
Top Scorer
Didier Drogba
Player of the Year
Didier Drogba
 
 
 
 
2012/13
Manager
André Villas-Boas
Rafael Benítez
Captain
John Terry
Most Appearances
Juan Mata
Oscar
Fernando Torres
Top Scorer
Fernando Torres
Player of the Year
Juan Mata
 
 
2015/16
Manager
José Mourinho
Guus Hiddink
Captain
John Terry
Most Appearances
César Azpilicueta
Willian
Top Scorer
Diego Costa
Player of the Year
Willian
 
 
2018/19
Manager
Maurizio Sarri
Captain
Gary Cahill
Most Appearances
César Azpilicueta
Top Scorer
Eden Hazard
Player of the Year
Eden Hazard
 
 
2021/22
Manager
Thomas Tuchel
Captain
César Azpilicueta
Most Appearances
Antonio Rüdiger
Top Scorer
Romelu Lukaku
Player of the Year
Mason Mount
 
 
 
 
 
 
2024/25
Manager
Enzo Maresca
Captain
Reece James
Most Appearances
Moisés Caicedo
Cole Palmer
Top Scorer
Cole Palmer
Player of the Year
Moisés Caicedo
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