| 1 | Sat 2 Dec | 61-2 v UxbridgeUxbridge 2-1 Chipstead | Isthmian League - South Central Division |
| 2 | Tue 26 Dec | 17 1-4 v South Park (Reigate)Chipstead 1-4 South Park (Reigate) | Isthmian League - South Central Division |
| 3 | Mon 1 Jan | 51-0 v Corinthian-CasualsCorinthian-Casuals 0-1 Chipstead | Isthmian League - South Central Division |
| 4 | Tue 9 Jan | 5 0-1 v SouthallChipstead 0-1 Southall | Isthmian League - South Central Division |
| 5 | Sat 13 Jan | 52-2 v Ashford Town (Middx)Chipstead 2-2 Ashford Town (Middx) | Isthmian League - South Central Division |
| 6 | Tue 23 Jan | 5 1-2 v Badshot LeaBadshot Lea 2-1 Chipstead | Velocity Cup Fourth Round |
| 7 | Sat 27 Jan | 50-2 v Metropolitan PoliceChipstead 0-2 Metropolitan Police | Isthmian League - South Central Division |
| 8 | Wed 31 Jan | 53-5 v GuernseyGuernsey 5-3 Chipstead | Isthmian League - South Central Division |
| 9 | Sat 3 Feb | 50-0 v Badshot LeaChipstead 0-0 Badshot Lea | Isthmian League - South Central Division |
| 10 | Tue 6 Feb | 51-2 v MarlowChipstead 1-2 Marlow | Isthmian League - South Central Division |
| 11 | Sat 10 Feb | 50-1 v Ascot UnitedAscot United 1-0 Chipstead | Isthmian League - South Central Division |
| 12 | Tue 13 Feb | 51-2 v Raynes Park ValeRaynes Park Vale 2-1 Chipstead | Isthmian League - South Central Division |
| 13 | Sat 17 Feb | 5 1-2 v Chertsey TownChipstead 1-2 Chertsey Town | Isthmian League - South Central Division |
| 14 | Sat 24 Feb | 50-4 v MarlowMarlow 4-0 Chipstead | Isthmian League - South Central Division |
| 15 | Tue 27 Feb | 51-1 v LeatherheadLeatherhead 1-1 Chipstead | Isthmian League - South Central Division |
| 16 | Sat 16 Mar | 52-0 v UxbridgeChipstead 2-0 Uxbridge | Isthmian League - South Central Division |
| 17 | Tue 19 Mar | 50-1 v WestfieldChipstead 0-1 Westfield | Isthmian League - South Central Division |
| 18 | Sat 23 Mar | 50-2 v Sutton Common RoversSutton Common Rovers 2-0 Chipstead | Isthmian League - South Central Division |
| 19 | Sat 30 Mar | 50-5 v BinfieldChipstead 0-5 Binfield | Isthmian League - South Central Division |
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