1. Round | 07/08/1999 | Tranmere Rovers | - | Bolton Wanderers | 0:0 | ||||
2. Round | 14/08/1999 | Bolton Wanderers | - | Queens Park Rangers | 2:1 | ||||
3. Round | 21/08/1999 | Ipswich Town | - | Bolton Wanderers | 1:0 | ||||
4. Round | 28/08/1999 | Bolton Wanderers | - | Manchester City | 0:1 | ||||
6. Round | 05/09/1999 | Bolton Wanderers | - | Birmingham City | 3:3 | ||||
7. Round | 11/09/1999 | Charlton Athletic | - | Bolton Wanderers | 2:1 | ||||
8. Round | 18/09/1999 | Bolton Wanderers | - | Barnsley FC | 2:2 | ||||
9. Round | 25/09/1999 | Bolton Wanderers | - | Nottingham Forest | 3:2 | ||||
10. Round | 02/10/1999 | Swindon Town | - | Bolton Wanderers | 0:4 | ||||
11. Round | 09/10/1999 | Wolverhampton Wanderers | - | Bolton Wanderers | 1:0 | ||||
12. Round | 16/10/1999 | Bolton Wanderers | - | Huddersfield Town | 1:0 | ||||
13. Round | 19/10/1999 | Bolton Wanderers | - | Crewe Alexandra | 2:2 | ||||
14. Round | 24/10/1999 | Norwich City | - | Bolton Wanderers | 2:1 | ||||
15. Round | 27/10/1999 | Nottingham Forest | - | Bolton Wanderers | 1:1 | ||||
16. Round | 30/10/1999 | Bolton Wanderers | - | Swindon Town | 2:0 |