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Chelsea matches where Gordon Strachan was opposition manager/coach
| Date | Venue | Opponent | Score | Comp |
| 09/04/1997 | Highfield Road | Coventry City | 1-3 | Premier League |
| 09/08/1997 | Highfield Road | Coventry City | 2-3 | Premier League |
| 10/01/1998 | Stamford Bridge | Coventry City | 3-1 | Premier League |
| 15/08/1998 | Highfield Road | Coventry City | 1-2 | Premier League |
| 16/01/1999 | Stamford Bridge | Coventry City | 2-1 | Premier League |
| 04/01/2000 | Highfield Road | Coventry City | 2-2 | Premier League |
| 12/04/2000 | Stamford Bridge | Coventry City | 2-1 | Premier League |
| 21/10/2000 | Stamford Bridge | Coventry City | 6-1 | Premier League |
| 03/03/2001 | Highfield Road | Coventry City | 0-0 | Premier League |
| 01/01/2002 | Stamford Bridge | Southampton | 2-4 | Premier League |
| 28/08/2002 | St Mary's Stadium | Southampton | 1-1 | Premier League |
| 26/12/2002 | Stamford Bridge | Southampton | 0-0 | Premier League |
| 22/11/2003 | St Mary's Stadium | Southampton | 1-0 | Premier League |