| 17. Round | 21/11/2009 | Morecambe FC | - | Cheltenham Town | 1:0 |  |
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| 18. Round | 24/11/2009 | Cheltenham Town | - | Barnet FC | 5:1 | ||||
| 19. Round | 01/12/2009 | Torquay United | - | Cheltenham Town | 3:0 | |
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| 21. Round | 12/12/2009 | Chesterfield FC | - | Cheltenham Town | 1:0 | |
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| 23. Round | 26/12/2009 | Cheltenham Town | - | AFC Bournemouth | 0:1 | ||||
| 24. Round | 28/12/2009 | Dagenham & Redbridge | - | Cheltenham Town | 0:2 | ||||
| 25. Round | 02/01/2010 | Bradford City | - | Cheltenham Town | 1:1 | |
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| 27. Round | 16/01/2010 | Grimsby Town | - | Cheltenham Town | 0:0 | ||||
| 28. Round | 23/01/2010 | Cheltenham Town | - | Rochdale AFC | 1:4 | ||||
| 30. Round | 06/02/2010 | AFC Bournemouth | - | Cheltenham Town | 0:0 | ||||
| 22. Round | 09/02/2010 | Cheltenham Town | - | Burton Albion | 0:1 | |
England