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Chelsea matches where Steve McClaren was opposition manager/coach
| Date | Venue | Opponent | Score | Comp |
| 23/09/2001 | Stamford Bridge | Middlesbrough | 2-2 | Premier League |
| 27/04/2002 | Riverside Stadium | Middlesbrough | 2-0 | Premier League |
| 16/11/2002 | Stamford Bridge | Middlesbrough | 1-0 | Premier League |
| 14/12/2002 | Riverside Stadium | Middlesbrough | 1-1 | Premier League |
| 04/01/2003 | Stamford Bridge | Middlesbrough | 1-0 | F.A. Cup |
| 05/10/2003 | Riverside Stadium | Middlesbrough | 2-1 | Premier League |
| 10/04/2004 | Stamford Bridge | Middlesbrough | 0-0 | Premier League |
| 25/09/2004 | Riverside Stadium | Middlesbrough | 1-0 | Premier League |
| 04/01/2005 | Stamford Bridge | Middlesbrough | 2-0 | Premier League |
| 03/12/2005 | Stamford Bridge | Middlesbrough | 1-0 | Premier League |
| 11/02/2006 | Riverside Stadium | Middlesbrough | 0-3 | Premier League |
| 05/01/2014 | iPro Stadium | Derby County | 2-0 | F.A. Cup |
| 16/12/2014 | iPro Stadium | Derby County | 3-1 | Capital One Cup |
| 26/09/2015 | St James' Park | Newcastle United | 2-2 | Premier League |
| 13/02/2016 | Stamford Bridge | Newcastle United | 5-1 | Premier League |