| 1 | Fri 28 Jul | 52-2 v Chesham UnitedChertsey Town 2-2 Chesham United | Friendly |
| 2 | Sat 12 Aug | 52-1 v Hanworth VillaChertsey Town 2-1 Hanworth Villa | Isthmian League - South Central Division |
| 3 | Sat 19 Aug | 53-1 v Snodland TownSnodland Town 1-3 Chertsey Town | Emirates FA Cup Preliminary Round |
| 4 | Sat 26 Aug | 50-0 v WestfieldWestfield 0-0 Chertsey Town | Isthmian League - South Central Division |
| 5 | Mon 28 Aug | 52-1 v Hartley WintneyChertsey Town 2-1 Hartley Wintney | Isthmian League - South Central Division |
| 6 | Sat 9 Sep | 51-1 v Hanworth VillaHanworth Villa 1-1 Chertsey Town | Isuzu FA Trophy First Qualifying Round |
| 7 | Sat 16 Sep | 52-3 v Raynes Park ValeRaynes Park Vale 3-2 Chertsey Town | Isthmian League - South Central Division |
| 8 | Sat 23 Sep | 5 2-4 v Hythe TownChertsey Town 2-4 Hythe Town | Isuzu FA Trophy Second Qualifying Round |
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