| 2. Round | 15/08/2015 | Port Vale FC | - | Gillingham FC | 1:1 | ||||
| 4. Round | 22/08/2015 | Gillingham FC | - | Wigan Athletic | 2:0 | ||||
| 12. Round | 10/10/2015 | Chesterfield FC | - | Gillingham FC | 1:3 | ||||
| 13. Round | 17/10/2015 | Crewe Alexandra | - | Gillingham FC | 0:1 |  |
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| 14. Round | 20/10/2015 | Gillingham FC | - | Scunthorpe United | 2:1 | ||||
| 15. Round | 24/10/2015 | Gillingham FC | - | Southend United | 1:1 | |
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| 16. Round | 31/10/2015 | Walsall FC | - | Gillingham FC | 3:2 | |
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| 21. Round | 12/12/2015 | Gillingham FC | - | Burton Albion | 0:3 | ||||
| 24. Round | 28/12/2015 | Gillingham FC | - | Colchester United | 1:0 | ||||
| 26. Round | 07/01/2016 | Wigan Athletic | - | Gillingham FC | 3:2 | |
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| 27. Round | 16/01/2016 | Doncaster Rovers | - | Gillingham FC | 2:2 | ||||
| 31. Round | 13/02/2016 | Gillingham FC | - | Barnsley FC | 2:1 | ||||
| 35. Round | 05/03/2016 | Scunthorpe United | - | Gillingham FC | 0:0 | ||||
| 36. Round | 12/03/2016 | Gillingham FC | - | Crewe Alexandra | 3:0 | ||||
| 37. Round | 19/03/2016 | Southend United | - | Gillingham FC | 1:1 | |
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| 42. Round | 16/04/2016 | Gillingham FC | - | Port Vale FC | 0:2 | ||||
| 43. Round | 19/04/2016 | Rochdale AFC | - | Gillingham FC | 1:1 |
England
Grenada