2. Round | 14/08/1999 | Wolverhampton Wanderers | - | Portsmouth FC | 1:1 | ||||
3. Round | 21/08/1999 | Portsmouth FC | - | Stockport County | 2:0 | ||||
4. Round | 28/08/1999 | Barnsley FC | - | Portsmouth FC | 6:0 | ||||
5. Round | 30/08/1999 | Portsmouth FC | - | Huddersfield Town | 0:0 | ||||
7. Round | 11/09/1999 | Portsmouth FC | - | Ipswich Town | 1:1 | ||||
8. Round | 18/09/1999 | Tranmere Rovers | - | Portsmouth FC | 2:4 | ||||
9. Round | 25/09/1999 | Portsmouth FC | - | Grimsby Town | 1:2 | ||||
10. Round | 02/10/1999 | Crystal Palace | - | Portsmouth FC | 4:0 | ||||
12. Round | 16/10/1999 | Portsmouth FC | - | Charlton Athletic | 0:2 | ||||
13. Round | 19/10/1999 | Portsmouth FC | - | Walsall FC | 5:1 | ||||
14. Round | 23/10/1999 | Queens Park Rangers | - | Portsmouth FC | 0:0 | ||||
15. Round | 26/10/1999 | Grimsby Town | - | Portsmouth FC | 1:0 | ||||
16. Round | 30/10/1999 | Portsmouth FC | - | Crystal Palace | 3:1 | ||||
11. Round | 03/11/1999 | Manchester City | - | Portsmouth FC | 4:2 | ||||
17. Round | 06/11/1999 | Portsmouth FC | - | Birmingham City | 2:2 | ||||
6. Round | 09/11/1999 | Fulham FC | - | Portsmouth FC | 1:0 | ||||
27. Round | 15/01/2000 | Portsmouth FC | - | Wolverhampton Wanderers | 2:3 |