| 28. Round | 15/01/1999 | Grimsby Town | - | Oxford United | 1:0 |  |
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| 29. Round | 29/01/1999 | Oxford United | - | Barnsley FC | 1:0 | ||||
| 31. Round | 12/02/1999 | Oxford United | - | Swindon Town | 2:0 | ||||
| 33. Round | 26/02/1999 | Oxford United | - | Sunderland AFC | 0:0 | ||||
| 34. Round | 02/03/1999 | Queens Park Rangers | - | Oxford United | 1:0 | ||||
| 35. Round | 05/03/1999 | West Bromwich Albion | - | Oxford United | 2:0 | |
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| 36. Round | 08/03/1999 | Oxford United | - | Huddersfield Town | 2:2 | |
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| 37. Round | 12/03/1999 | Oxford United | - | Watford FC | 0:0 | ||||
| 38. Round | 19/03/1999 | Crewe Alexandra | - | Oxford United | 3:1 | ||||
| 39. Round | 25/03/1999 | Sheffield United | - | Oxford United | 1:2 | ||||
| 40. Round | 02/04/1999 | Oxford United | - | Bolton Wanderers | 0:0 | ||||
| 41. Round | 04/04/1999 | Tranmere Rovers | - | Oxford United | 2:2 | ||||
| 42. Round | 09/04/1999 | Oxford United | - | Bury FC | 0:1 | ||||
| 43. Round | 16/04/1999 | Port Vale FC | - | Oxford United | 1:0 | |
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| 44. Round | 23/04/1999 | Oxford United | - | Norwich City | 2:4 | ||||
| 45. Round | 30/04/1999 | Bradford City | - | Oxford United | 0:0 | ||||
| 46. Round | 08/05/1999 | Oxford United | - | Stockport County | 5:0 |
England