| 1 | Fri 28 Jul | 62-2 v Chesham UnitedChertsey Town 2-2 Chesham United | Friendly |
| 2 | Sat 12 Aug | 62-1 v Hanworth VillaChertsey Town 2-1 Hanworth Villa | Isthmian League - South Central Division |
| 3 | Sat 19 Aug | 63-1 v Snodland TownSnodland Town 1-3 Chertsey Town | Emirates FA Cup Preliminary Round |
| 4 | Sat 26 Aug | 6 0-0 v WestfieldWestfield 0-0 Chertsey Town | Isthmian League - South Central Division |
| 5 | Mon 28 Aug | 62-1 v Hartley WintneyChertsey Town 2-1 Hartley Wintney | Isthmian League - South Central Division |
| 6 | Sat 2 Sep | 61-2 v Hayes & Yeading UnitedHayes & Yeading United 2-1 Chertsey Town | Emirates FA Cup First Qualifying Round |
| 7 | Sat 9 Sep | 81-1 v Hanworth VillaHanworth Villa 1-1 Chertsey Town | Isuzu FA Trophy First Qualifying Round |
| 8 | Sat 16 Sep | 7 2-3 v Raynes Park ValeRaynes Park Vale 3-2 Chertsey Town | Isthmian League - South Central Division |
| 9 | Tue 26 Sep | 82-1 v SouthallChertsey Town 2-1 Southall | Velocity Cup Second Round |
| 10 | Sat 30 Sep | 83-0 v Ashford Town (Middx)Ashford Town (Middx) 0-3 Chertsey Town | Isthmian League - South Central Division |
| 11 | Tue 3 Oct | 81-1 v BinfieldBinfield 1-1 Chertsey Town | Isthmian League - South Central Division |
| 12 | Sat 7 Oct | 42-1 v UxbridgeChertsey Town 2-1 Uxbridge | Isthmian League - South Central Division |
| 13 | Tue 10 Oct | 81-0 v LeatherheadLeatherhead 0-1 Chertsey Town | Isthmian League - South Central Division |
| 14 | Sat 14 Oct | 83-0 v Metropolitan PoliceChertsey Town 3-0 Metropolitan Police | Isthmian League - South Central Division |
| 15 | Sat 21 Oct | 74-2 v NorthwoodNorthwood 2-4 Chertsey Town | Isthmian League - South Central Division |
| 16 | Sat 28 Oct | 72-1 v ChipsteadChertsey Town 2-1 Chipstead | Isthmian League - South Central Division |
| 17 | Sat 4 Nov | 44-0 v South Park (Reigate)South Park (Reigate) 0-4 Chertsey Town | Isthmian League - South Central Division |
| 18 | Tue 7 Nov | 4 2-2 v WestfieldChertsey Town 2-2 Westfield | Velocity Cup Third Round |
| 19 | Tue 14 Nov | 41-1 v Walton & HershamWalton & Hersham 1-1 Chertsey Town | Surrey Senior Cup Second Round |
| 20 | Sat 2 Dec | 86-0 v Corinthian-CasualsCorinthian-Casuals 0-6 Chertsey Town | Isthmian League - South Central Division |
| 21 | Sat 16 Dec | 40-0 v Sutton Common RoversChertsey Town 0-0 Sutton Common Rovers | Isthmian League - South Central Division |
| 22 | Sat 23 Dec | 42-1 v Ascot UnitedAscot United 1-2 Chertsey Town | Isthmian League - South Central Division |
| 23 | Tue 26 Dec | 4 2-2 v Thatcham TownChertsey Town 2-2 Thatcham Town | Isthmian League - South Central Division |
| 24 | Sat 30 Dec | 49-0 v BinfieldChertsey Town 9-0 Binfield | Isthmian League - South Central Division |
| 25 | Mon 1 Jan | 43-1 v Hartley WintneyHartley Wintney 1-3 Chertsey Town | Isthmian League - South Central Division |
| 26 | Sat 13 Jan | 44-1 v Raynes Park ValeChertsey Town 4-1 Raynes Park Vale | Isthmian League - South Central Division |
| 27 | Sat 20 Jan | 46-0 v UxbridgeUxbridge 0-6 Chertsey Town | Isthmian League - South Central Division |
| 28 | Sat 27 Jan | 42-1 v Ashford Town (Middx)Chertsey Town 2-1 Ashford Town (Middx) | Isthmian League - South Central Division |
| 29 | Tue 30 Jan | 42-1 v LeatherheadChertsey Town 2-1 Leatherhead | Isthmian League - South Central Division |
| 30 | Sat 3 Feb | 41-0 v Metropolitan PoliceMetropolitan Police 0-1 Chertsey Town | Isthmian League - South Central Division |
| 31 | Tue 6 Feb | 42-0 v Badshot LeaBadshot Lea 0-2 Chertsey Town | Isthmian League - South Central Division |
| 32 | Sat 17 Feb | 42-1 v ChipsteadChipstead 1-2 Chertsey Town | Isthmian League - South Central Division |
| 33 | Tue 20 Feb | 4 1-0 v MarlowMarlow 0-1 Chertsey Town | Isthmian League - South Central Division |
| 34 | Sat 24 Feb | 44-4 v South Park (Reigate)Chertsey Town 4-4 South Park (Reigate) | Isthmian League - South Central Division |
| 35 | Tue 27 Feb | 42-2 v Sutton Common RoversChertsey Town 2-2 Sutton Common Rovers | Surrey Senior Cup Third Round |
| 36 | Sat 9 Mar | 40-0 v NorthwoodChertsey Town 0-0 Northwood | Isthmian League - South Central Division |
| 37 | Wed 13 Mar | 46-2 v GuernseyGuernsey 2-6 Chertsey Town | Isthmian League - South Central Division |
| 38 | Sat 16 Mar | 44-1 v Corinthian-CasualsChertsey Town 4-1 Corinthian-Casuals | Isthmian League - South Central Division |
| 39 | Tue 19 Mar | 41-0 v MarlowChertsey Town 1-0 Marlow | Isthmian League - South Central Division |
| 40 | Sat 23 Mar | 4 3-0 v SouthallSouthall 0-3 Chertsey Town | Isthmian League - South Central Division |
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