| 1. Round | 13/08/2005 | Portsmouth FC | - | Tottenham Hotspur | 0:2 | ||||
| 2. Round | 20/08/2005 | West Bromwich Albion | - | Portsmouth FC | 2:1 |  |
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| 3. Round | 23/08/2005 | Portsmouth FC | - | Aston Villa | 1:1 | ||||
| 4. Round | 27/08/2005 | Manchester City | - | Portsmouth FC | 2:1 | ||||
| 5. Round | 10/09/2005 | Everton FC | - | Portsmouth FC | 0:1 | ||||
| 6. Round | 17/09/2005 | Portsmouth FC | - | Birmingham City | 1:1 | ||||
| 7. Round | 24/09/2005 | Bolton Wanderers | - | Portsmouth FC | 1:0 | ||||
| 20. Round | 31/12/2005 | Portsmouth FC | - | Fulham FC | 1:0 | |
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| 21. Round | 02/01/2006 | Blackburn Rovers | - | Portsmouth FC | 2:1 | ||||
| 22. Round | 14/01/2006 | Portsmouth FC | - | Everton FC | 0:1 | ||||
| 23. Round | 21/01/2006 | Birmingham City | - | Portsmouth FC | 5:0 | ||||
| 24. Round | 01/02/2006 | Portsmouth FC | - | Bolton Wanderers | 1:1 |  |
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| 27. Round | 25/02/2006 | Chelsea FC | - | Portsmouth FC | 2:0 | ||||
| 28. Round | 04/03/2006 | Aston Villa | - | Portsmouth FC | 1:0 | |
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| 32. Round | 01/04/2006 | Fulham FC | - | Portsmouth FC | 1:3 | ||||
| 34. Round | 15/04/2006 | Portsmouth FC | - | Middlesbrough FC | 1:0 | ||||
| 35. Round | 17/04/2006 | Charlton Athletic | - | Portsmouth FC | 2:1 | |
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