| 27. Round | 05/01/2019 | Macclesfield Town | - | Swindon Town | 1:2 |  |
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| 28. Round | 12/01/2019 | Swindon Town | - | Lincoln City | 2:2 | ||||
| 29. Round | 19/01/2019 | Tranmere Rovers | - | Swindon Town | 1:2 | ||||
| 30. Round | 26/01/2019 | Swindon Town | - | Crawley Town | 0:1 | ||||
| 32. Round | 09/02/2019 | Milton Keynes Dons | - | Swindon Town | 2:3 | ||||
| 31. Round | 12/02/2019 | Swindon Town | - | Forest Green Rovers | 2:0 | |
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| 34. Round | 23/02/2019 | Swindon Town | - | Grimsby Town | 1:1 | ||||
| 35. Round | 02/03/2019 | Swindon Town | - | Colchester United | 3:0 |  |
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| 36. Round | 09/03/2019 | Carlisle United | - | Swindon Town | 2:1 | |
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| 37. Round | 12/03/2019 | Stevenage FC | - | Swindon Town | 2:0 | ||||
| 38. Round | 16/03/2019 | Swindon Town | - | Port Vale FC | 0:0 | ||||
| 39. Round | 23/03/2019 | Swindon Town | - | Morecambe FC | 4:0 | ||||
| 40. Round | 30/03/2019 | Bury FC | - | Swindon Town | 1:3 | |
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| 41. Round | 06/04/2019 | Swindon Town | - | Yeovil Town | 1:1 | ||||
| 33. Round | 09/04/2019 | Newport County | - | Swindon Town | 0:0 | |
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| 45. Round | 27/04/2019 | Cheltenham Town | - | Swindon Town | 3:2 | ||||
| 46. Round | 04/05/2019 | Swindon Town | - | Notts County | 3:1 |
Ireland