| 1 | Fri 28 Jul | 92-2 v Chesham UnitedChertsey Town 2-2 Chesham United | Friendly |
| 2 | Sat 12 Aug | 92-1 v Hanworth VillaChertsey Town 2-1 Hanworth Villa | Isthmian League - South Central Division |
| 3 | Sat 19 Aug | 93-1 v Snodland TownSnodland Town 1-3 Chertsey Town | Emirates FA Cup Preliminary Round |
| 4 | Sat 26 Aug | 90-0 v WestfieldWestfield 0-0 Chertsey Town | Isthmian League - South Central Division |
| 5 | Mon 28 Aug | 162-1 v Hartley WintneyChertsey Town 2-1 Hartley Wintney | Isthmian League - South Central Division |
| 6 | Sat 2 Sep | 91-2 v Hayes & Yeading UnitedHayes & Yeading United 2-1 Chertsey Town | Emirates FA Cup First Qualifying Round |
| 7 | Sat 9 Sep | 151-1 v Hanworth VillaHanworth Villa 1-1 Chertsey Town | Isuzu FA Trophy First Qualifying Round |
| 8 | Sat 16 Sep | 152-3 v Raynes Park ValeRaynes Park Vale 3-2 Chertsey Town | Isthmian League - South Central Division |
| 9 | Sat 23 Sep | 92-4 v Hythe TownChertsey Town 2-4 Hythe Town | Isuzu FA Trophy Second Qualifying Round |
| 10 | Tue 26 Sep | 92-1 v SouthallChertsey Town 2-1 Southall | Velocity Cup Second Round |
| 11 | Sat 30 Sep | 93-0 v Ashford Town (Middx)Ashford Town (Middx) 0-3 Chertsey Town | Isthmian League - South Central Division |
| 12 | Tue 3 Oct | 91-1 v BinfieldBinfield 1-1 Chertsey Town | Isthmian League - South Central Division |
| 13 | Sat 7 Oct | 92-1 v UxbridgeChertsey Town 2-1 Uxbridge | Isthmian League - South Central Division |
| 14 | Tue 10 Oct | 141-0 v LeatherheadLeatherhead 0-1 Chertsey Town | Isthmian League - South Central Division |
| 15 | Sat 28 Oct | 142-1 v ChipsteadChertsey Town 2-1 Chipstead | Isthmian League - South Central Division |
| 16 | Sat 4 Nov | 164-0 v South Park (Reigate)South Park (Reigate) 0-4 Chertsey Town | Isthmian League - South Central Division |
| 17 | Tue 7 Nov | 92-2 v WestfieldChertsey Town 2-2 Westfield | Velocity Cup Third Round |
| 18 | Tue 14 Nov | 121-1 v Walton & HershamWalton & Hersham 1-1 Chertsey Town | Surrey Senior Cup Second Round |
| 19 | Tue 21 Nov | 124-1 v GuernseyChertsey Town 4-1 Guernsey | Isthmian League - South Central Division |
| 20 | Sat 25 Nov | 122-1 v SouthallChertsey Town 2-1 Southall | Isthmian League - South Central Division |
| 21 | Sat 2 Dec | 126-0 v Corinthian-CasualsCorinthian-Casuals 0-6 Chertsey Town | Isthmian League - South Central Division |
| 22 | Sat 16 Dec | 120-0 v Sutton Common RoversChertsey Town 0-0 Sutton Common Rovers | Isthmian League - South Central Division |
| 23 | Sat 23 Dec | 142-1 v Ascot UnitedAscot United 1-2 Chertsey Town | Isthmian League - South Central Division |
| 24 | Tue 26 Dec | 92-2 v Thatcham TownChertsey Town 2-2 Thatcham Town | Isthmian League - South Central Division |
| 25 | Sat 30 Dec | 159-0 v BinfieldChertsey Town 9-0 Binfield | Isthmian League - South Central Division |
| 26 | Mon 1 Jan | 143-1 v Hartley WintneyHartley Wintney 1-3 Chertsey Town | Isthmian League - South Central Division |
| 27 | Sat 13 Jan | 154-1 v Raynes Park ValeChertsey Town 4-1 Raynes Park Vale | Isthmian League - South Central Division |
| 28 | Sat 20 Jan | 156-0 v UxbridgeUxbridge 0-6 Chertsey Town | Isthmian League - South Central Division |
| 29 | Sat 27 Jan | 152-1 v Ashford Town (Middx)Chertsey Town 2-1 Ashford Town (Middx) | Isthmian League - South Central Division |
| 30 | Tue 30 Jan | 152-1 v LeatherheadChertsey Town 2-1 Leatherhead | Isthmian League - South Central Division |
| 31 | Sat 3 Feb | 161-0 v Metropolitan PoliceMetropolitan Police 0-1 Chertsey Town | Isthmian League - South Central Division |
| 32 | Tue 6 Feb | 92-0 v Badshot LeaBadshot Lea 0-2 Chertsey Town | Isthmian League - South Central Division |
| 33 | Tue 20 Feb | 141-0 v MarlowMarlow 0-1 Chertsey Town | Isthmian League - South Central Division |
| 34 | Sat 24 Feb | 154-4 v South Park (Reigate)Chertsey Town 4-4 South Park (Reigate) | Isthmian League - South Central Division |
| 35 | Tue 27 Feb | 92-2 v Sutton Common RoversChertsey Town 2-2 Sutton Common Rovers | Surrey Senior Cup Third Round |
| 36 | Wed 13 Mar | 156-2 v GuernseyGuernsey 2-6 Chertsey Town | Isthmian League - South Central Division |
| 37 | Sat 23 Mar | 153-0 v SouthallSouthall 0-3 Chertsey Town | Isthmian League - South Central Division |
| 38 | Mon 1 Apr | 121-1 v Thatcham TownThatcham Town 1-1 Chertsey Town | Isthmian League - South Central Division |
| 39 | Sat 6 Apr | 122-1 v Hanworth VillaHanworth Villa 1-2 Chertsey Town | Isthmian League - South Central Division |
| 40 | Tue 9 Apr | 9 3-2 v South Park (Reigate)Chertsey Town 3-2 South Park (Reigate) | Surrey Senior Cup Fourth Round |
| 41 | Sat 13 Apr | 153-1 v Ascot UnitedChertsey Town 3-1 Ascot United | Isthmian League - South Central Division |
| 42 | Sat 20 Apr | 152-0 v Sutton Common RoversSutton Common Rovers 0-2 Chertsey Town | Isthmian League - South Central Division |
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