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Chelsea matches where Jack Crayston was opposition manager/coach
| Date | Venue | Opponent | Score | Comp |
| 25/12/1956 | Stamford Bridge | Arsenal | 1-1 | Football League Division 1 |
| 26/12/1956 | Highbury | Arsenal | 0-2 | Football League Division 1 |
| 26/10/1957 | Stamford Bridge | Arsenal | 0-0 | Football League Division 1 |
| 08/03/1958 | Highbury | Arsenal | 4-5 | Football League Division 1 |