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Chelsea matches where James Howie was opposition manager/coach
| Date | Venue | Opponent | Score | Comp |
| 23/04/1921 | Ayresome Park | Middlesbrough | 0-0 | Football League Division 1 |
| 30/04/1921 | Stamford Bridge | Middlesbrough | 1-1 | Football League Division 1 |
| 26/12/1921 | Ayresome Park | Middlesbrough | 1-0 | Football League Division 1 |
| 27/12/1921 | Stamford Bridge | Middlesbrough | 1-1 | Football League Division 1 |
| 09/09/1922 | Stamford Bridge | Middlesbrough | 1-1 | Football League Division 1 |
| 16/09/1922 | Ayresome Park | Middlesbrough | 1-2 | Football League Division 1 |