| 1. Round | 07/08/1999 | Crystal Palace | - | Crewe Alexandra | 1:1 |  |
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| 2. Round | 14/08/1999 | Barnsley FC | - | Crystal Palace | 2:3 |  |
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| 3. Round | 21/08/1999 | Crystal Palace | - | Swindon Town | 1:2 | ||||
| 4. Round | 28/08/1999 | Huddersfield Town | - | Crystal Palace | 7:1 | ||||
| 6. Round | 04/09/1999 | Sheffield United | - | Crystal Palace | 3:1 | ||||
| 7. Round | 11/09/1999 | Manchester City | - | Crystal Palace | 2:1 | |
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| 8. Round | 18/09/1999 | Crystal Palace | - | Grimsby Town | 3:0 | ||||
| 9. Round | 25/09/1999 | West Bromwich Albion | - | Crystal Palace | 0:0 | ||||
| 5. Round | 28/09/1999 | Crystal Palace | - | Wolverhampton Wanderers | 1:1 | |
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| 10. Round | 02/10/1999 | Crystal Palace | - | Portsmouth FC | 4:0 |
England