| 1. Round | 26/08/1988 | Sheffield Wednesday | - | Luton Town | 1:0 | ||||
| 4. Round | 16/09/1988 | Luton Town | - | Manchester United | 0:2 | ||||
| 5. Round | 23/09/1988 | Everton FC | - | Luton Town | 0:2 | ||||
| 6. Round | 01/10/1988 | Nottingham Forest | - | Luton Town | 0:0 | ||||
| 7. Round | 08/10/1988 | Luton Town | - | Liverpool FC | 1:0 | ||||
| 9. Round | 22/10/1988 | Middlesbrough FC | - | Luton Town | 2:1 | ||||
| 10. Round | 28/10/1988 | Luton Town | - | Queens Park Rangers | 0:0 | ||||
| 11. Round | 04/11/1988 | Millwall FC | - | Luton Town | 3:1 | ||||
| 22. Round | 20/01/1989 | Luton Town | - | Everton FC | 1:0 | ||||
| 23. Round | 03/02/1989 | Luton Town | - | Nottingham Forest | 2:3 | ||||
| 28. Round | 10/03/1989 | Luton Town | - | Millwall FC | 1:2 | ||||
| 32. Round | 31/03/1989 | Aston Villa | - | Luton Town | 2:1 | ||||
| 34. Round | 14/04/1989 | Luton Town | - | Coventry City | 2:2 |  |
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| 35. Round | 21/04/1989 | Newcastle United | - | Luton Town | 0:0 | ||||
| 36. Round | 28/04/1989 | Luton Town | - | Derby County | 3:0 | ||||
| 33. Round | 01/05/1989 | Luton Town | - | Charlton Athletic | 5:2 | ||||
| 37. Round | 05/05/1989 | West Ham United | - | Luton Town | 1:0 | ||||
| 38. Round | 12/05/1989 | Luton Town | - | Norwich City | 1:0 |
England