2. Ronde | 14.08.1999 | Wolverhampton Wanderers | - | Portsmouth FC | 1:1 | ||||
3. Ronde | 21.08.1999 | Portsmouth FC | - | Stockport County | 2:0 | ||||
4. Ronde | 28.08.1999 | Barnsley FC | - | Portsmouth FC | 6:0 | ||||
5. Ronde | 30.08.1999 | Portsmouth FC | - | Huddersfield Town | 0:0 | ||||
7. Ronde | 11.09.1999 | Portsmouth FC | - | Ipswich Town | 1:1 | ||||
8. Ronde | 18.09.1999 | Tranmere Rovers | - | Portsmouth FC | 2:4 | ||||
9. Ronde | 25.09.1999 | Portsmouth FC | - | Grimsby Town | 1:2 | ||||
10. Ronde | 02.10.1999 | Crystal Palace | - | Portsmouth FC | 4:0 | ||||
12. Ronde | 16.10.1999 | Portsmouth FC | - | Charlton Athletic | 0:2 | ||||
13. Ronde | 19.10.1999 | Portsmouth FC | - | Walsall FC | 5:1 | ||||
14. Ronde | 23.10.1999 | Queens Park Rangers | - | Portsmouth FC | 0:0 | ||||
15. Ronde | 26.10.1999 | Grimsby Town | - | Portsmouth FC | 1:0 | ||||
16. Ronde | 30.10.1999 | Portsmouth FC | - | Crystal Palace | 3:1 | ||||
11. Ronde | 03.11.1999 | Manchester City | - | Portsmouth FC | 4:2 | ||||
17. Ronde | 06.11.1999 | Portsmouth FC | - | Birmingham City | 2:2 | ||||
6. Ronde | 09.11.1999 | Fulham FC | - | Portsmouth FC | 1:0 | ||||
27. Ronde | 15.01.2000 | Portsmouth FC | - | Wolverhampton Wanderers | 2:3 |