| 31. Jornada | 02.02.2019 | Coventry City | - | Gillingham FC | 1:1 | ||||
| 33. Jornada | 16.02.2019 | Gillingham FC | - | Scunthorpe United | 1:0 | ||||
| 30. Jornada | 19.02.2019 | Sunderland | - | Gillingham FC | 4:2 |  |
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| 34. Jornada | 23.02.2019 | Wycombe Wanderers | - | Gillingham FC | 0:1 | ||||
| 35. Jornada | 02.03.2019 | Fleetwood Town | - | Gillingham FC | 1:1 | |
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| 36. Jornada | 09.03.2019 | Gillingham FC | - | Oxford United | 1:0 | ||||
| 37. Jornada | 12.03.2019 | Gillingham FC | - | Bristol Rovers | 0:1 | ||||
| 38. Jornada | 16.03.2019 | Luton Town | - | Gillingham FC | 2:2 | ||||
| 39. Jornada | 23.03.2019 | AFC Wimbledon | - | Gillingham FC | 2:4 |  |
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| 40. Jornada | 30.03.2019 | Gillingham FC | - | Rochdale AFC | 1:1 | ||||
| 41. Jornada | 06.04.2019 | Peterborough United | - | Gillingham FC | 2:0 | ||||
| 44. Jornada | 22.04.2019 | Bradford City | - | Gillingham FC | 1:1 | ||||
| 45. Jornada | 27.04.2019 | Gillingham FC | - | Charlton Athletic | 0:2 | ||||
| 46. Jornada | 04.05.2019 | Blackpool FC | - | Gillingham FC | 0:3 | |
Portugal