| 1 | Sat 16 Dec | 80-3 v Thatcham TownThatcham Town 3-0 Chipstead | Isthmian League - South Central Division |
| 2 | Sat 23 Dec | 81-3 v Hanworth VillaHanworth Villa 3-1 Chipstead | Isthmian League - South Central Division |
| 3 | Tue 26 Dec | 81-4 v South Park (Reigate)Chipstead 1-4 South Park (Reigate) | Isthmian League - South Central Division |
| 4 | Tue 23 Jan | 81-2 v Badshot LeaBadshot Lea 2-1 Chipstead | Velocity Cup Fourth Round |
| 5 | Sat 10 Feb | 120-1 v Ascot UnitedAscot United 1-0 Chipstead | Isthmian League - South Central Division |
| 6 | Tue 13 Feb | 71-2 v Raynes Park ValeRaynes Park Vale 2-1 Chipstead | Isthmian League - South Central Division |
| 7 | Sat 17 Feb | 71-2 v Chertsey TownChipstead 1-2 Chertsey Town | Isthmian League - South Central Division |
| 8 | Sat 24 Feb | 70-4 v MarlowMarlow 4-0 Chipstead | Isthmian League - South Central Division |
| 9 | Tue 27 Feb | 71-1 v LeatherheadLeatherhead 1-1 Chipstead | Isthmian League - South Central Division |
| 10 | Sat 16 Mar | 82-0 v UxbridgeChipstead 2-0 Uxbridge | Isthmian League - South Central Division |
| 11 | Tue 19 Mar | 80-1 v WestfieldChipstead 0-1 Westfield | Isthmian League - South Central Division |
| 12 | Sat 23 Mar | 80-2 v Sutton Common RoversSutton Common Rovers 2-0 Chipstead | Isthmian League - South Central Division |
| 13 | Sat 30 Mar | 70-5 v BinfieldChipstead 0-5 Binfield | Isthmian League - South Central Division |
| 14 | Mon 1 Apr | 71-2 v South Park (Reigate)South Park (Reigate) 2-1 Chipstead | Isthmian League - South Central Division |
| 15 | Sat 6 Apr | 72-0 v Hartley WintneyHartley Wintney 0-2 Chipstead | Isthmian League - South Central Division |
| 16 | Sat 13 Apr | 70-0 v Hanworth VillaChipstead 0-0 Hanworth Villa | Isthmian League - South Central Division |
| 17 | Sat 20 Apr | 70-3 v Thatcham TownChipstead 0-3 Thatcham Town | Isthmian League - South Central Division |
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