| 1. Round | 12/08/2000 | Sheffield United | - | Portsmouth FC | 2:0 |  |
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| 2. Round | 19/08/2000 | Portsmouth FC | - | Grimsby Town | 1:1 | ||||
| 3. Round | 25/08/2000 | Gillingham FC | - | Portsmouth FC | 1:1 | ||||
| 4. Round | 28/08/2000 | Portsmouth FC | - | Wolverhampton Wanderers | 3:1 | ||||
| 5. Round | 02/09/2000 | Preston North End | - | Portsmouth FC | 1:0 | ||||
| 6. Round | 09/09/2000 | Portsmouth FC | - | Watford FC | 1:3 | |
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| 7. Round | 12/09/2000 | Portsmouth FC | - | Tranmere Rovers | 2:0 | ||||
| 8. Round | 16/09/2000 | Bolton Wanderers | - | Portsmouth FC | 2:0 | ||||
| 11. Round | 08/10/2000 | Stockport County | - | Portsmouth FC | 1:1 | ||||
| 12. Round | 14/10/2000 | Portsmouth FC | - | Sheffield Wednesday | 2:1 | ||||
| 13. Round | 17/10/2000 | Portsmouth FC | - | Crewe Alexandra | 2:1 | ||||
| 14. Round | 21/10/2000 | Crystal Palace | - | Portsmouth FC | 2:3 | ||||
| 15. Round | 24/10/2000 | Norwich City | - | Portsmouth FC | 0:0 | |
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| 16. Round | 28/10/2000 | Portsmouth FC | - | Birmingham City | 1:1 | |
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| 20. Round | 25/11/2000 | Barnsley FC | - | Portsmouth FC | 1:0 | ||||
| 21. Round | 02/12/2000 | Portsmouth FC | - | Norwich City | 2:0 | ||||
| 22. Round | 09/12/2000 | Nottingham Forest | - | Portsmouth FC | 2:0 |
England