| 1. Round | 16/08/1998 | Southampton FC | - | Liverpool FC | 1:2 | ||||
| 2. Round | 22/08/1998 | Liverpool FC | - | Arsenal FC | 0:0 | ||||
| 3. Round | 30/08/1998 | Newcastle United | - | Liverpool FC | 1:4 | ||||
| 5. Round | 12/09/1998 | West Ham United | - | Liverpool FC | 2:1 | ||||
| 6. Round | 19/09/1998 | Liverpool FC | - | Charlton Athletic | 3:3 | ||||
| 7. Round | 24/09/1998 | Manchester United | - | Liverpool FC | 2:0 | ||||
| 8. Round | 04/10/1998 | Liverpool FC | - | Chelsea FC | 1:1 | ||||
| 9. Round | 17/10/1998 | Everton FC | - | Liverpool FC | 0:0 | ||||
| 10. Round | 24/10/1998 | Liverpool FC | - | Nottingham Forest | 5:1 | ||||
| 11. Round | 31/10/1998 | Leicester City | - | Liverpool FC | 1:0 |  |
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| 12. Round | 07/11/1998 | Liverpool FC | - | Derby County | 1:2 | ||||
| 14. Round | 21/11/1998 | Aston Villa | - | Liverpool FC | 2:4 | ||||
| 20. Round | 28/12/1998 | Liverpool FC | - | Newcastle United | 4:2 |
England