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Chelsea matches where Andy Aitken was opposition manager/coach
| Date | Venue | Opponent | Score | Comp |
| 26/12/1907 | Stamford Bridge | Middlesbrough | 1-0 | Football League Division 1 |
| 01/01/1908 | Ayresome Park | Middlesbrough | 1-3 | Football League Division 1 |
| 01/01/1909 | Ayresome Park | Middlesbrough | 4-1 | Football League Division 1 |
| 29/04/1909 | Stamford Bridge | Leicester Fosse | 1-0 | Football League Division 1 |
| 17/09/1910 | Filbert Street | Leicester Fosse | 0-1 | Football League Division 2 |
| 21/01/1911 | Stamford Bridge | Leicester Fosse | 2-0 | Football League Division 2 |