| 1 | Fri 28 Jul | 22-2 v Chesham UnitedChertsey Town 2-2 Chesham United | Friendly |
| 2 | Sat 12 Aug | 22-1 v Hanworth VillaChertsey Town 2-1 Hanworth Villa | Isthmian League - South Central Division |
| 3 | Sat 19 Aug | 7 3-1 v Snodland TownSnodland Town 1-3 Chertsey Town | Emirates FA Cup Preliminary Round |
| 4 | Sat 26 Aug | 2 0-0 v WestfieldWestfield 0-0 Chertsey Town | Isthmian League - South Central Division |
| 5 | Mon 28 Aug | 22-1 v Hartley WintneyChertsey Town 2-1 Hartley Wintney | Isthmian League - South Central Division |
| 6 | Sat 2 Sep | 21-2 v Hayes & Yeading UnitedHayes & Yeading United 2-1 Chertsey Town | Emirates FA Cup First Qualifying Round |
| 7 | Sat 9 Sep | 21-1 v Hanworth VillaHanworth Villa 1-1 Chertsey Town | Isuzu FA Trophy First Qualifying Round |
| 8 | Sat 16 Sep | 2 2-3 v Raynes Park ValeRaynes Park Vale 3-2 Chertsey Town | Isthmian League - South Central Division |
| 9 | Sat 23 Sep | 22-4 v Hythe TownChertsey Town 2-4 Hythe Town | Isuzu FA Trophy Second Qualifying Round |
| 10 | Tue 7 Nov | 152-2 v WestfieldChertsey Town 2-2 Westfield | Velocity Cup Third Round |
| 11 | Sat 3 Feb | 111-0 v Metropolitan PoliceMetropolitan Police 0-1 Chertsey Town | Isthmian League - South Central Division |
| 12 | Wed 13 Mar | 116-2 v GuernseyGuernsey 2-6 Chertsey Town | Isthmian League - South Central Division |
| 13 | Sat 16 Mar | 11 4-1 v Corinthian-CasualsChertsey Town 4-1 Corinthian-Casuals | Isthmian League - South Central Division |
| 14 | Tue 19 Mar | 11 1-0 v MarlowChertsey Town 1-0 Marlow | Isthmian League - South Central Division |
| 15 | Sat 23 Mar | 113-0 v SouthallSouthall 0-3 Chertsey Town | Isthmian League - South Central Division |
| 16 | Sat 30 Mar | 111-1 v WestfieldChertsey Town 1-1 Westfield | Isthmian League - South Central Division |
| 17 | Mon 1 Apr | 111-1 v Thatcham TownThatcham Town 1-1 Chertsey Town | Isthmian League - South Central Division |
| 18 | Sat 6 Apr | 112-1 v Hanworth VillaHanworth Villa 1-2 Chertsey Town | Isthmian League - South Central Division |
| 19 | Tue 9 Apr | 23-2 v South Park (Reigate)Chertsey Town 3-2 South Park (Reigate) | Surrey Senior Cup Fourth Round |
| 20 | Sat 13 Apr | 23-1 v Ascot UnitedChertsey Town 3-1 Ascot United | Isthmian League - South Central Division |
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