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Chelsea matches where David Calderhead(Snr) was opposition manager/coach
| Date | Venue | Opponent | Score | Comp |
| 14/10/1905 | Sincil Bank | Lincoln City | 4-1 | Football League Division 2 |
| 17/02/1906 | Stamford Bridge | Lincoln City | 4-2 | Football League Division 2 |
| 13/10/1906 | Stamford Bridge | Lincoln City | 2-0 | Football League Division 2 |
| 12/01/1907 | Sincil Bank | Lincoln City | 2-2 | F.A. Cup |
| 16/01/1907 | Stamford Bridge | Lincoln City | 0-1 | F.A. Cup |
| 16/02/1907 | Sincil Bank | Lincoln City | 5-0 | Football League Division 2 |