1. Round | 07/08/1999 | Crystal Palace | - | Crewe Alexandra | 1:1 | ||||
2. Round | 14/08/1999 | Barnsley FC | - | Crystal Palace | 2:3 | ||||
3. Round | 21/08/1999 | Crystal Palace | - | Swindon Town | 1:2 | ||||
4. Round | 28/08/1999 | Huddersfield Town | - | Crystal Palace | 7:1 | ||||
8. Round | 18/09/1999 | Crystal Palace | - | Grimsby Town | 3:0 | ||||
10. Round | 02/10/1999 | Crystal Palace | - | Portsmouth FC | 4:0 | ||||
22. Round | 04/12/1999 | Crewe Alexandra | - | Crystal Palace | 2:0 | ||||
11. Round | 08/12/1999 | Crystal Palace | - | Ipswich Town | 2:2 | ||||
24. Round | 26/12/1999 | Charlton Athletic | - | Crystal Palace | 2:1 | ||||
46. Round | 07/05/2000 | Tranmere Rovers | - | Crystal Palace | 1:2 |