| 1. Ronde | 07.08.1999 | Crystal Palace | - | Crewe Alexandra | 1:1 | ||||
| 3. Ronde | 21.08.1999 | Crystal Palace | - | Swindon Town | 1:2 | ||||
| 6. Ronde | 04.09.1999 | Sheffield United | - | Crystal Palace | 3:1 | ||||
| 7. Ronde | 11.09.1999 | Manchester City | - | Crystal Palace | 2:1 | ||||
| 5. Ronde | 28.09.1999 | Crystal Palace | - | Wolverhampton Wanderers | 1:1 |  |
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| 18. Ronde | 14.11.1999 | Crystal Palace | - | Queens Park Rangers | 3:0 | ||||
| 19. Ronde | 20.11.1999 | Port Vale FC | - | Crystal Palace | 2:2 | ||||
| 21. Ronde | 27.11.1999 | Crystal Palace | - | Nottingham Forest | 2:0 | ||||
| 22. Ronde | 04.12.1999 | Crewe Alexandra | - | Crystal Palace | 2:0 | ||||
| 11. Ronde | 08.12.1999 | Crystal Palace | - | Ipswich Town | 2:2 | ||||
| 24. Ronde | 26.12.1999 | Charlton Athletic | - | Crystal Palace | 2:1 | ||||
| 30. Ronde | 05.02.2000 | Wolverhampton Wanderers | - | Crystal Palace | 2:1 | ||||
| 31. Ronde | 12.02.2000 | Crystal Palace | - | Sheffield United | 1:1 | ||||
| 32. Ronde | 19.02.2000 | Nottingham Forest | - | Crystal Palace | 2:0 | ||||
| 33. Ronde | 26.02.2000 | Grimsby Town | - | Crystal Palace | 1:0 | ||||
| 35. Ronde | 07.03.2000 | Crystal Palace | - | Bolton Wanderers | 0:0 |
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