1. Round | 07/08/1999 | Walsall FC | - | Swindon Town | 0:0 | ||||
2. Round | 15/08/1999 | Swindon Town | - | Ipswich Town | 1:4 | ||||
3. Round | 21/08/1999 | Crystal Palace | - | Swindon Town | 1:2 | ||||
4. Round | 28/08/1999 | Swindon Town | - | West Bromwich Albion | 1:2 | ||||
5. Round | 30/08/1999 | Grimsby Town | - | Swindon Town | 1:0 | ||||
8. Round | 18/09/1999 | Crewe Alexandra | - | Swindon Town | 2:1 | ||||
9. Round | 25/09/1999 | Port Vale FC | - | Swindon Town | 2:0 | ||||
6. Round | 28/09/1999 | Swindon Town | - | Blackburn Rovers | 2:1 | ||||
10. Round | 02/10/1999 | Swindon Town | - | Bolton Wanderers | 0:4 | ||||
11. Round | 09/10/1999 | Swindon Town | - | Stockport County | 1:1 | ||||
12. Round | 16/10/1999 | Fulham FC | - | Swindon Town | 1:0 | ||||
13. Round | 19/10/1999 | Barnsley FC | - | Swindon Town | 1:0 | ||||
14. Round | 23/10/1999 | Swindon Town | - | Sheffield United | 2:2 |