| 1 | Sat 16 Sep | 3 1-1 v Ashford Town (Middx)Ashford Town (Middx) 1-1 Chipstead | Isthmian League - South Central Division |
| 2 | Sat 23 Sep | 31-4 v Raynes Park ValeChipstead 1-4 Raynes Park Vale | Isthmian League - South Central Division |
| 3 | Tue 26 Sep | 31-0 v LeatherheadLeatherhead 0-1 Chipstead | Velocity Cup Second Round |
| 4 | Sat 30 Sep | 30-4 v Metropolitan PoliceMetropolitan Police 4-0 Chipstead | Isthmian League - South Central Division |
| 5 | Sat 7 Oct | 31-0 v NorthwoodNorthwood 0-1 Chipstead | Isthmian League - South Central Division |
| 6 | Tue 10 Oct | 34-1 v GuernseyChipstead 4-1 Guernsey | Isthmian League - South Central Division |
| 7 | Sat 14 Oct | 3 2-4 v Badshot LeaBadshot Lea 4-2 Chipstead | Isthmian League - South Central Division |
| 8 | Sat 21 Oct | 31-0 v Ascot UnitedChipstead 1-0 Ascot United | Isthmian League - South Central Division |
| 9 | Sat 28 Oct | 3 1-2 v Chertsey TownChertsey Town 2-1 Chipstead | Isthmian League - South Central Division |
| 10 | Tue 31 Oct | 122-2 v South Park (Reigate)South Park (Reigate) 2-2 Chipstead | Velocity Cup Third Round |
| 11 | Tue 7 Nov | 30-4 v LeatherheadChipstead 0-4 Leatherhead | Isthmian League - South Central Division |
| 12 | Sat 11 Nov | 31-3 v NorthwoodChipstead 1-3 Northwood | Isthmian League - South Central Division |
| 13 | Sat 18 Nov | 151-3 v WestfieldWestfield 3-1 Chipstead | Isthmian League - South Central Division |
| 14 | Sat 25 Nov | 32-3 v Sutton Common RoversChipstead 2-3 Sutton Common Rovers | Isthmian League - South Central Division |
| 15 | Sat 2 Dec | 31-2 v UxbridgeUxbridge 2-1 Chipstead | Isthmian League - South Central Division |
| 16 | Sat 16 Dec | 30-3 v Thatcham TownThatcham Town 3-0 Chipstead | Isthmian League - South Central Division |
| 17 | Sat 23 Dec | 31-3 v Hanworth VillaHanworth Villa 3-1 Chipstead | Isthmian League - South Central Division |
| 18 | Tue 26 Dec | 31-4 v South Park (Reigate)Chipstead 1-4 South Park (Reigate) | Isthmian League - South Central Division |
| 19 | Mon 1 Jan | 31-0 v Corinthian-CasualsCorinthian-Casuals 0-1 Chipstead | Isthmian League - South Central Division |
| 20 | Tue 9 Jan | 30-1 v SouthallChipstead 0-1 Southall | Isthmian League - South Central Division |
| 21 | Sat 13 Jan | 32-2 v Ashford Town (Middx)Chipstead 2-2 Ashford Town (Middx) | Isthmian League - South Central Division |
| 22 | Tue 23 Jan | 31-2 v Badshot LeaBadshot Lea 2-1 Chipstead | Velocity Cup Fourth Round |
| 23 | Sat 27 Jan | 30-2 v Metropolitan PoliceChipstead 0-2 Metropolitan Police | Isthmian League - South Central Division |
| 24 | Wed 31 Jan | 33-5 v GuernseyGuernsey 5-3 Chipstead | Isthmian League - South Central Division |
| 25 | Tue 6 Feb | 31-2 v MarlowChipstead 1-2 Marlow | Isthmian League - South Central Division |
| 26 | Sat 10 Feb | 30-1 v Ascot UnitedAscot United 1-0 Chipstead | Isthmian League - South Central Division |
| 27 | Tue 13 Feb | 31-2 v Raynes Park ValeRaynes Park Vale 2-1 Chipstead | Isthmian League - South Central Division |
| 28 | Sat 17 Feb | 31-2 v Chertsey TownChipstead 1-2 Chertsey Town | Isthmian League - South Central Division |
| 29 | Sat 24 Feb | 30-4 v MarlowMarlow 4-0 Chipstead | Isthmian League - South Central Division |
| 30 | Tue 27 Feb | 31-1 v LeatherheadLeatherhead 1-1 Chipstead | Isthmian League - South Central Division |
| 31 | Sat 16 Mar | 32-0 v UxbridgeChipstead 2-0 Uxbridge | Isthmian League - South Central Division |
| 32 | Tue 19 Mar | 3 0-1 v WestfieldChipstead 0-1 Westfield | Isthmian League - South Central Division |
| 33 | Sat 23 Mar | 30-2 v Sutton Common RoversSutton Common Rovers 2-0 Chipstead | Isthmian League - South Central Division |
| 34 | Sat 30 Mar | 30-5 v BinfieldChipstead 0-5 Binfield | Isthmian League - South Central Division |
| 35 | Mon 1 Apr | 31-2 v South Park (Reigate)South Park (Reigate) 2-1 Chipstead | Isthmian League - South Central Division |
| 36 | Sat 6 Apr | 15 2-0 v Hartley WintneyHartley Wintney 0-2 Chipstead | Isthmian League - South Central Division |
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