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Chelsea matches where Reg Freeman was opposition manager/coach
| Date | Venue | Opponent | Score | Comp |
| 05/09/1953 | Stamford Bridge | Sheffield United | 1-2 | Football League Division 1 |
| 16/01/1954 | Bramall Lane | Sheffield United | 3-1 | Football League Division 1 |
| 20/09/1954 | Bramall Lane | Sheffield United | 2-1 | Football League Division 1 |
| 08/04/1955 | Stamford Bridge | Sheffield United | 1-1 | Football League Division 1 |