| 1 | Sat 16 Sep | 171-1 v Ashford Town (Middx)Ashford Town (Middx) 1-1 Chipstead | Isthmian League - South Central Division |
| 2 | Sat 23 Sep | 171-4 v Raynes Park ValeChipstead 1-4 Raynes Park Vale | Isthmian League - South Central Division |
| 3 | Tue 26 Sep | 71-0 v LeatherheadLeatherhead 0-1 Chipstead | Velocity Cup Second Round |
| 4 | Sat 30 Sep | 10 0-4 v Metropolitan PoliceMetropolitan Police 4-0 Chipstead | Isthmian League - South Central Division |
| 5 | Sat 2 Dec | 171-2 v UxbridgeUxbridge 2-1 Chipstead | Isthmian League - South Central Division |
| 6 | Sat 16 Dec | 10 0-3 v Thatcham TownThatcham Town 3-0 Chipstead | Isthmian League - South Central Division |
| 7 | Sat 23 Dec | 61-3 v Hanworth VillaHanworth Villa 3-1 Chipstead | Isthmian League - South Central Division |
| 8 | Tue 26 Dec | 6 1-4 v South Park (Reigate)Chipstead 1-4 South Park (Reigate) | Isthmian League - South Central Division |
| 9 | Mon 1 Jan | 6 1-0 v Corinthian-CasualsCorinthian-Casuals 0-1 Chipstead | Isthmian League - South Central Division |
| 10 | Tue 9 Jan | 60-1 v SouthallChipstead 0-1 Southall | Isthmian League - South Central Division |
| 11 | Sat 13 Jan | 62-2 v Ashford Town (Middx)Chipstead 2-2 Ashford Town (Middx) | Isthmian League - South Central Division |
| 12 | Sat 27 Jan | 80-2 v Metropolitan PoliceChipstead 0-2 Metropolitan Police | Isthmian League - South Central Division |
| 13 | Wed 31 Jan | 143-5 v GuernseyGuernsey 5-3 Chipstead | Isthmian League - South Central Division |
| 14 | Sat 3 Feb | 6 0-0 v Badshot LeaChipstead 0-0 Badshot Lea | Isthmian League - South Central Division |
| 15 | Tue 6 Feb | 8 1-2 v MarlowChipstead 1-2 Marlow | Isthmian League - South Central Division |
| 16 | Sat 10 Feb | 60-1 v Ascot UnitedAscot United 1-0 Chipstead | Isthmian League - South Central Division |
| 17 | Tue 13 Feb | 61-2 v Raynes Park ValeRaynes Park Vale 2-1 Chipstead | Isthmian League - South Central Division |
| 18 | Sat 17 Feb | 61-2 v Chertsey TownChipstead 1-2 Chertsey Town | Isthmian League - South Central Division |
| 19 | Sat 24 Feb | 6 0-4 v MarlowMarlow 4-0 Chipstead | Isthmian League - South Central Division |
| 20 | Tue 27 Feb | 61-1 v LeatherheadLeatherhead 1-1 Chipstead | Isthmian League - South Central Division |
| 21 | Tue 19 Mar | 40-1 v WestfieldChipstead 0-1 Westfield | Isthmian League - South Central Division |
| 22 | Sat 23 Mar | 40-2 v Sutton Common RoversSutton Common Rovers 2-0 Chipstead | Isthmian League - South Central Division |
| 23 | Sat 30 Mar | 80-5 v BinfieldChipstead 0-5 Binfield | Isthmian League - South Central Division |
| 24 | Mon 1 Apr | 61-2 v South Park (Reigate)South Park (Reigate) 2-1 Chipstead | Isthmian League - South Central Division |
| 25 | Sat 6 Apr | 6 2-0 v Hartley WintneyHartley Wintney 0-2 Chipstead | Isthmian League - South Central Division |
| 26 | Sat 13 Apr | 60-0 v Hanworth VillaChipstead 0-0 Hanworth Villa | Isthmian League - South Central Division |
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