1. Round | 07/08/1999 | Portsmouth FC | - | Sheffield United | 2:0 | ||||
18. Round | 14/11/1999 | West Bromwich Albion | - | Portsmouth FC | 3:2 | ||||
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 | ||||
23. Round | 18/12/1999 | Portsmouth FC | - | Port Vale FC | 0:0 | ||||
24. Round | 26/12/1999 | Swindon Town | - | Portsmouth FC | 1:1 | ||||
25. Round | 28/12/1999 | Portsmouth FC | - | Blackburn Rovers | 1:2 | ||||
38. Round | 21/03/2000 | Portsmouth FC | - | West Bromwich Albion | 2:0 |