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Chelsea matches where Bryan Robson was opposition manager/coach
| Date | Venue | Opponent | Score | Comp |
| 26/08/1995 | Riverside Stadium | Middlesbrough | 0-2 | Premier League |
| 04/02/1996 | Stamford Bridge | Middlesbrough | 5-0 | Premier League |
| 21/08/1996 | Stamford Bridge | Middlesbrough | 1-0 | Premier League |
| 22/03/1997 | Riverside Stadium | Middlesbrough | 0-1 | Premier League |
| 17/05/1997 | Wembley | Middlesbrough | 2-0 | F.A. Cup |
| 29/03/1998 | Wembley | Middlesbrough | 2-0 | Coca Cola Cup |
| 26/09/1998 | Stamford Bridge | Middlesbrough | 2-0 | Premier League |
| 14/04/1999 | Riverside Stadium | Middlesbrough | 0-0 | Premier League |
| 25/09/1999 | Riverside Stadium | Middlesbrough | 1-0 | Premier League |
| 22/04/2000 | Stamford Bridge | Middlesbrough | 1-1 | Premier League |
| 15/03/2005 | Stamford Bridge | West Bromwich Albion | 1-0 | Premier League |
| 24/08/2005 | Stamford Bridge | West Bromwich Albion | 4-0 | Premier League |
| 04/03/2006 | The Hawthorns | West Bromwich Albion | 2-1 | Premier League |