| 3. Round | 21/08/1999 | Walsall FC | - | Crewe Alexandra | 1:4 | ||||
| 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 | ||||
| 8. Round | 18/09/1999 | Walsall FC | - | Manchester City | 0:1 | ||||
| 9. Round | 25/09/1999 | Blackburn Rovers | - | Walsall FC | 2:0 | ||||
| 18. Round | 12/11/1999 | Walsall FC | - | Port Vale FC | 0:0 | ||||
| 21. Round | 26/11/1999 | Walsall FC | - | Fulham FC | 1:3 | ||||
| 23. Round | 18/12/1999 | Barnsley FC | - | Walsall FC | 3:2 | ||||
| 24. Round | 26/12/1999 | Walsall FC | - | Tranmere Rovers | 1:2 | ||||
| 35. Round | 07/03/2000 | Walsall FC | - | Charlton Athletic | 2:4 | ||||
| 36. Round | 11/03/2000 | Huddersfield Town | - | Walsall FC | 1:1 |  |
|||
| 37. Round | 18/03/2000 | Walsall FC | - | Queens Park Rangers | 2:3 |
Iceland