| 1 | Fri 28 Jul | 112-2 v Chesham UnitedChertsey Town 2-2 Chesham United | Friendly |
| 2 | Sat 12 Aug | 142-1 v Hanworth VillaChertsey Town 2-1 Hanworth Villa | Isthmian League - South Central Division |
| 3 | Sat 26 Aug | 160-0 v WestfieldWestfield 0-0 Chertsey Town | Isthmian League - South Central Division |
| 4 | Mon 28 Aug | 92-1 v Hartley WintneyChertsey Town 2-1 Hartley Wintney | Isthmian League - South Central Division |
| 5 | Sat 2 Sep | 101-2 v Hayes & Yeading UnitedHayes & Yeading United 2-1 Chertsey Town | Emirates FA Cup First Qualifying Round |
| 6 | Sat 9 Sep | 91-1 v Hanworth VillaHanworth Villa 1-1 Chertsey Town | Isuzu FA Trophy First Qualifying Round |
| 7 | Sat 16 Sep | 92-3 v Raynes Park ValeRaynes Park Vale 3-2 Chertsey Town | Isthmian League - South Central Division |
| 8 | Sat 30 Sep | 14 3-0 v Ashford Town (Middx)Ashford Town (Middx) 0-3 Chertsey Town | Isthmian League - South Central Division |
| 9 | Sat 14 Oct | 17 3-0 v Metropolitan PoliceChertsey Town 3-0 Metropolitan Police | Isthmian League - South Central Division |
| 10 | Sat 21 Oct | 164-2 v NorthwoodNorthwood 2-4 Chertsey Town | Isthmian League - South Central Division |
| 11 | Sat 28 Oct | 162-1 v ChipsteadChertsey Town 2-1 Chipstead | Isthmian League - South Central Division |
| 12 | Sat 4 Nov | 174-0 v South Park (Reigate)South Park (Reigate) 0-4 Chertsey Town | Isthmian League - South Central Division |
| 13 | Tue 7 Nov | 122-2 v WestfieldChertsey Town 2-2 Westfield | Velocity Cup Third Round |
| 14 | Sat 25 Nov | 142-1 v SouthallChertsey Town 2-1 Southall | Isthmian League - South Central Division |
| 15 | Sat 2 Dec | 146-0 v Corinthian-CasualsCorinthian-Casuals 0-6 Chertsey Town | Isthmian League - South Central Division |
| 16 | Sat 16 Dec | 140-0 v Sutton Common RoversChertsey Town 0-0 Sutton Common Rovers | Isthmian League - South Central Division |
| 17 | Sat 23 Dec | 92-1 v Ascot UnitedAscot United 1-2 Chertsey Town | Isthmian League - South Central Division |
| 18 | Tue 26 Dec | 122-2 v Thatcham TownChertsey Town 2-2 Thatcham Town | Isthmian League - South Central Division |
| 19 | Sat 30 Dec | 179-0 v BinfieldChertsey Town 9-0 Binfield | Isthmian League - South Central Division |
| 20 | Sat 13 Jan | 174-1 v Raynes Park ValeChertsey Town 4-1 Raynes Park Vale | Isthmian League - South Central Division |
| 21 | Sat 20 Jan | 166-0 v UxbridgeUxbridge 0-6 Chertsey Town | Isthmian League - South Central Division |
| 22 | Sat 27 Jan | 82-1 v Ashford Town (Middx)Chertsey Town 2-1 Ashford Town (Middx) | Isthmian League - South Central Division |
| 23 | Tue 30 Jan | 172-1 v LeatherheadChertsey Town 2-1 Leatherhead | Isthmian League - South Central Division |
| 24 | Sat 3 Feb | 121-0 v Metropolitan PoliceMetropolitan Police 0-1 Chertsey Town | Isthmian League - South Central Division |
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