| Name | Period | Trophies |
|---|---|---|
 Ted Drake | 1952–1961 | First Division Championship, Charity Shield |
 Tommy Docherty | 1962–1967 | League Cup |
| Dave Sexton | 1967–1974 | FA Cup, UEFA Cup Winners' Cup |
| John Neal | 1981–1985 | Second Division Championship |
| John Hollins | 1985–1988 | Full Members Cup |
| Bobby Campbell | 1988–1991 | Second Division Championship, Full Members Cup |
 Ruud Gullit | 1996–1998 | FA Cup |
 Gianluca Vialli | 1998–2000 | FA Cup, League Cup, Charity Shield, UEFA Cup Winners' Cup, UEFA Super Cup |
 José Mourinho | 2004–2007 | 2 Premier Leagues, 2 League Cups, FA Cup, Community Shield |
| Guus Hiddink | 2009 | FA Cup |
| Carlo Ancelotti | 2009– | Premier League, FA Cup, Community Shield |
Coaching staff
| Position | Staff |
|---|---|
| Manager | Carlo Ancelotti |
| Assistant First Team Coach | Bruno DeMichelis |
| Assistant First Team Coach | Paul Clement |
| Assistant First Team Coach |  Michael Emenalo |
| Goalkeeper Coach |  Christophe Lollichon |
| First Team Fitness Coach | Glen Driscoll |
| Individual Team Fitness Coach | Giovanni Mauri |
| Assistant First Team Fitness Coach | Chris Jones |
| Senior Opposition Scout | Mick McGiven |
| Medical Director | Dr. Bryan English |
| Sporting Director and Director of Youth Development |  Frank Arnesen |
| Reserve Team Manager | Steve Holland |
| Youth Team Manager | Dermot Drummy |
| Academy Manager | Neil Bath |
| Match Analyst | James Melbourne |
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