| 16. Round | 30/10/1999 | Bolton Wanderers | - | Swindon Town | 2:0 | ||||
| 27. Round | 15/01/2000 | Ipswich Town | - | Swindon Town | 3:0 | ||||
| 29. Round | 29/01/2000 | West Bromwich Albion | - | Swindon Town | 1:1 | ||||
| 31. Round | 12/02/2000 | Blackburn Rovers | - | Swindon Town | 0:0 | ||||
| 32. Round | 19/02/2000 | Swindon Town | - | Birmingham City | 1:4 | ||||
| 33. Round | 26/02/2000 | Swindon Town | - | Crewe Alexandra | 0:1 |  |
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| 34. Round | 04/03/2000 | Nottingham Forest | - | Swindon Town | 3:1 | ||||
| 35. Round | 07/03/2000 | Swindon Town | - | Huddersfield Town | 2:0 | ||||
| 36. Round | 11/03/2000 | Charlton Athletic | - | Swindon Town | 0:1 |  |
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| 37. Round | 18/03/2000 | Swindon Town | - | Wolverhampton Wanderers | 1:2 | ||||
| 38. Round | 22/03/2000 | Norwich City | - | Swindon Town | 0:2 | ||||
| 39. Round | 25/03/2000 | Portsmouth FC | - | Swindon Town | 4:1 | ||||
| 40. Round | 01/04/2000 | Swindon Town | - | Manchester City | 0:2 | ||||
| 42. Round | 15/04/2000 | Swindon Town | - | Tranmere Rovers | 3:1 | ||||
| 43. Round | 22/04/2000 | Swindon Town | - | Fulham FC | 1:0 | ||||
| 45. Round | 29/04/2000 | Swindon Town | - | Barnsley FC | 1:2 | ||||
| 46. Round | 07/05/2000 | Sheffield United | - | Swindon Town | 2:2 |
England