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Chelsea matches where John Gregory was opposition manager/coach
| Date | Venue | Opponent | Score | Comp |
| 13/05/1989 | Fratton Park | Portsmouth | 3-2 | Football League Division 2 |
| 08/03/1998 | Stamford Bridge | Aston Villa | 0-1 | Premier League |
| 28/10/1998 | Stamford Bridge | Aston Villa | 4-1 | Worthington Cup |
| 09/12/1998 | Stamford Bridge | Aston Villa | 2-1 | Premier League |
| 21/03/1999 | Villa Park | Aston Villa | 3-0 | Premier League |
| 21/08/1999 | Stamford Bridge | Aston Villa | 1-0 | Premier League |
| 22/01/2000 | Villa Park | Aston Villa | 0-0 | Premier League |
| 20/05/2000 | Wembley | Aston Villa | 1-0 | F.A. Cup |
| 27/08/2000 | Villa Park | Aston Villa | 1-1 | Premier League |
| 01/01/2001 | Stamford Bridge | Aston Villa | 1-0 | Premier League |
| 30/03/2002 | Stamford Bridge | Derby County | 2-1 | Premier League |