| 1 | Fri 28 Jul | 82-2 v Chesham UnitedChertsey Town 2-2 Chesham United | Friendly |
| 2 | Sat 12 Aug | 7 2-1 v Hanworth VillaChertsey Town 2-1 Hanworth Villa | Isthmian League - South Central Division |
| 3 | Sat 19 Aug | 123-1 v Snodland TownSnodland Town 1-3 Chertsey Town | Emirates FA Cup Preliminary Round |
| 4 | Sat 26 Aug | 70-0 v WestfieldWestfield 0-0 Chertsey Town | Isthmian League - South Central Division |
| 5 | Mon 28 Aug | 142-1 v Hartley WintneyChertsey Town 2-1 Hartley Wintney | Isthmian League - South Central Division |
| 6 | Sat 2 Sep | 51-2 v Hayes & Yeading UnitedHayes & Yeading United 2-1 Chertsey Town | Emirates FA Cup First Qualifying Round |
| 7 | Sat 23 Sep | 82-4 v Hythe TownChertsey Town 2-4 Hythe Town | Isuzu FA Trophy Second Qualifying Round |
| 8 | Tue 26 Sep | 152-1 v SouthallChertsey Town 2-1 Southall | Velocity Cup Second Round |
| 9 | Sat 30 Sep | 153-0 v Ashford Town (Middx)Ashford Town (Middx) 0-3 Chertsey Town | Isthmian League - South Central Division |
| 10 | Tue 3 Oct | 71-1 v BinfieldBinfield 1-1 Chertsey Town | Isthmian League - South Central Division |
| 11 | Sat 7 Oct | 152-1 v UxbridgeChertsey Town 2-1 Uxbridge | Isthmian League - South Central Division |
| 12 | Sat 21 Oct | 15 4-2 v NorthwoodNorthwood 2-4 Chertsey Town | Isthmian League - South Central Division |
| 13 | Sat 4 Nov | 124-0 v South Park (Reigate)South Park (Reigate) 0-4 Chertsey Town | Isthmian League - South Central Division |
| 14 | Tue 7 Nov | 72-2 v WestfieldChertsey Town 2-2 Westfield | Velocity Cup Third Round |
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