| 1 | Sat 7 Sep | 63-3 v Winchester CityChertsey Town 3-3 Winchester City | Southern League - Premier South |
| 2 | Sat 14 Sep | 62-0 v Hanwell TownHanwell Town 0-2 Chertsey Town | Emirates FA Cup Second Qualifying Round |
| 3 | Sat 28 Sep | 5 3-2 v Ashford UnitedChertsey Town 3-2 Ashford United | Emirates FA Cup Third Qualifying Round |
| 4 | Sat 5 Oct | 61-1 v Billericay TownChertsey Town 1-1 Billericay Town | Isuzu FA Trophy Third Qualifying Round |
| 5 | Sat 26 Oct | 63-0 v UxbridgeUxbridge 0-3 Chertsey Town | Isuzu FA Trophy First Round |
| 6 | Tue 5 Nov | 64-1 v Camberley TownCamberley Town 1-4 Chertsey Town | Surrey Senior Cup First Round |
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