| 1. Round | 07/08/1999 | Walsall FC | - | Swindon Town | 0:0 | ||||
| 2. Round | 14/08/1999 | Sheffield United | - | Walsall FC | 1:1 | ||||
| 3. Round | 21/08/1999 | Walsall FC | - | Crewe Alexandra | 1:4 | ||||
| 4. Round | 28/08/1999 | Wolverhampton Wanderers | - | Walsall FC | 1:2 | ||||
| 5. Round | 30/08/1999 | Walsall FC | - | Norwich City | 2:2 | ||||
| 6. Round | 04/09/1999 | Nottingham Forest | - | Walsall FC | 4:1 | ||||
| 7. Round | 11/09/1999 | Grimsby Town | - | Walsall FC | 1:0 | ||||
| 9. Round | 25/09/1999 | Blackburn Rovers | - | Walsall FC | 2:0 | ||||
| 10. Round | 02/10/1999 | Walsall FC | - | Stockport County | 1:2 | ||||
| 11. Round | 08/10/1999 | Walsall FC | - | Birmingham City | 1:0 | ||||
| 12. Round | 16/10/1999 | West Bromwich Albion | - | Walsall FC | 0:1 | ||||
| 13. Round | 19/10/1999 | Portsmouth FC | - | Walsall FC | 5:1 |  |
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| 14. Round | 23/10/1999 | Walsall FC | - | Ipswich Town | 0:1 | ||||
| 15. Round | 26/10/1999 | Walsall FC | - | Blackburn Rovers | 1:1 | ||||
| 16. Round | 30/10/1999 | Stockport County | - | Walsall FC | 1:1 | ||||
| 17. Round | 06/11/1999 | Charlton Athletic | - | Walsall FC | 2:1 | ||||
| 18. Round | 12/11/1999 | Walsall FC | - | Port Vale FC | 0:0 | |
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| 19. Round | 20/11/1999 | Queens Park Rangers | - | Walsall FC | 2:1 |
England