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Chelsea matches where John Bentley was opposition manager/coach
| Date | Venue | Opponent | Score | Comp |
| 25/12/1912 | Stamford Bridge | Manchester United | 1-4 | Football League Division 1 |
| 26/12/1912 | Old Trafford | Manchester United | 2-4 | Football League Division 1 |
| 20/09/1913 | Stamford Bridge | Manchester United | 0-2 | Football League Division 1 |
| 17/01/1914 | Old Trafford | Manchester United | 1-0 | Football League Division 1 |
| 31/10/1914 | Old Trafford | Manchester United | 2-2 | Football League Division 1 |