19. Ronde | 20.11.1999 | Portsmouth FC | - | Crewe Alexandra | 0:2 | ||||
20. Ronde | 24.11.1999 | Nottingham Forest | - | Portsmouth FC | 2:0 | ||||
21. Ronde | 27.11.1999 | Portsmouth FC | - | Bolton Wanderers | 0:0 | ||||
22. Ronde | 04.12.1999 | Sheffield United | - | Portsmouth FC | 1:0 |