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Chelsea matches where David O'Leary was opposition manager/coach
| Date | Venue | Opponent | Score | Comp |
| 25/10/1998 | Elland Road | Leeds United | 0-0 | Premier League |
| 05/05/1999 | Stamford Bridge | Leeds United | 1-0 | Premier League |
| 19/12/1999 | Stamford Bridge | Leeds United | 0-2 | Premier League |
| 01/04/2000 | Elland Road | Leeds United | 1-0 | Premier League |
| 12/11/2000 | Stamford Bridge | Leeds United | 1-1 | Premier League |
| 28/04/2001 | Elland Road | Leeds United | 0-2 | Premier League |
| 21/10/2001 | Elland Road | Leeds United | 0-0 | Premier League |
| 28/11/2001 | Elland Road | Leeds United | 2-0 | Worthington Cup |
| 30/01/2002 | Stamford Bridge | Leeds United | 2-0 | Premier League |
| 27/09/2003 | Stamford Bridge | Aston Villa | 1-0 | Premier League |
| 17/12/2003 | Villa Park | Aston Villa | 1-2 | Carling Cup |
| 12/04/2004 | Villa Park | Aston Villa | 2-3 | Premier League |
| 11/09/2004 | Villa Park | Aston Villa | 0-0 | Premier League |
| 26/12/2004 | Stamford Bridge | Aston Villa | 1-0 | Premier League |
| 24/09/2005 | Stamford Bridge | Aston Villa | 2-1 | Premier League |
| 01/02/2006 | Villa Park | Aston Villa | 1-1 | Premier League |