19. Round | 20/11/1999 | Portsmouth FC | - | Crewe Alexandra | 0:2 | ||||
20. Round | 24/11/1999 | Nottingham Forest | - | Portsmouth FC | 2:0 | ||||
21. Round | 27/11/1999 | Portsmouth FC | - | Bolton Wanderers | 0:0 | ||||
22. Round | 04/12/1999 | Sheffield United | - | Portsmouth FC | 1:0 |