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Chelsea matches where Jim Ryan was opposition manager/coach
| Date | Venue | Opponent | Score | Comp |
| 07/04/1990 | Stamford Bridge | Luton Town | 1-0 | Football League Division 1 |
| 29/12/1990 | Kenilworth Road | Luton Town | 0-2 | Football League Division 1 |
| 18/02/1991 | Stamford Bridge | Luton Town | 1-1 | Zenith Data Cup |
| 06/04/1991 | Stamford Bridge | Luton Town | 3-3 | Football League Division 1 |