| 1. Journée | 07.08.1999 | Walsall FC | - | Swindon Town | 0:0 | ||||
| 2. Journée | 15.08.1999 | Swindon Town | - | Ipswich Town | 1:4 | ||||
| 3. Journée | 21.08.1999 | Crystal Palace | - | Swindon Town | 1:2 | ||||
| 4. Journée | 28.08.1999 | Swindon Town | - | West Bromwich Albion | 1:2 |  |
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| 5. Journée | 30.08.1999 | Grimsby Town | - | Swindon Town | 1:0 | ||||
| 8. Journée | 18.09.1999 | Crewe Alexandra | - | Swindon Town | 2:1 | ||||
| 9. Journée | 25.09.1999 | Port Vale FC | - | Swindon Town | 2:0 | ||||
| 6. Journée | 28.09.1999 | Swindon Town | - | Blackburn Rovers | 2:1 | |
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| 10. Journée | 02.10.1999 | Swindon Town | - | Bolton Wanderers | 0:4 | |
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| 11. Journée | 09.10.1999 | Swindon Town | - | Stockport County | 1:1 | ||||
| 12. Journée | 16.10.1999 | Fulham FC | - | Swindon Town | 1:0 | ||||
| 13. Journée | 19.10.1999 | Barnsley FC | - | Swindon Town | 1:0 | ||||
| 14. Journée | 23.10.1999 | Swindon Town | - | Sheffield United | 2:2 |
Angleterre