| 1 | Tue 10 Oct | 154-1 v GuernseyChipstead 4-1 Guernsey | Isthmian League - South Central Division |
| 2 | Sat 14 Oct | 11 2-4 v Badshot LeaBadshot Lea 4-2 Chipstead | Isthmian League - South Central Division |
| 3 | Sat 21 Oct | 4 1-0 v Ascot UnitedChipstead 1-0 Ascot United | Isthmian League - South Central Division |
| 4 | Sat 28 Oct | 41-2 v Chertsey TownChertsey Town 2-1 Chipstead | Isthmian League - South Central Division |
| 5 | Tue 7 Nov | 40-4 v LeatherheadChipstead 0-4 Leatherhead | Isthmian League - South Central Division |
| 6 | Sat 11 Nov | 171-3 v NorthwoodChipstead 1-3 Northwood | Isthmian League - South Central Division |
| 7 | Sat 25 Nov | 162-3 v Sutton Common RoversChipstead 2-3 Sutton Common Rovers | Isthmian League - South Central Division |
| 8 | Sat 2 Dec | 7 1-2 v UxbridgeUxbridge 2-1 Chipstead | Isthmian League - South Central Division |
| 9 | Sat 16 Dec | 140-3 v Thatcham TownThatcham Town 3-0 Chipstead | Isthmian League - South Central Division |
| 10 | Sat 23 Dec | 141-3 v Hanworth VillaHanworth Villa 3-1 Chipstead | Isthmian League - South Central Division |
| 11 | Tue 26 Dec | 121-4 v South Park (Reigate)Chipstead 1-4 South Park (Reigate) | Isthmian League - South Central Division |
| 12 | Tue 23 Jan | 151-2 v Badshot LeaBadshot Lea 2-1 Chipstead | Velocity Cup Fourth Round |
| 13 | Sat 27 Jan | 160-2 v Metropolitan PoliceChipstead 0-2 Metropolitan Police | Isthmian League - South Central Division |
| 14 | Sat 16 Mar | 152-0 v UxbridgeChipstead 2-0 Uxbridge | Isthmian League - South Central Division |
| 15 | Tue 19 Mar | 150-1 v WestfieldChipstead 0-1 Westfield | Isthmian League - South Central Division |
| 16 | Sat 23 Mar | 150-2 v Sutton Common RoversSutton Common Rovers 2-0 Chipstead | Isthmian League - South Central Division |
| 17 | Sat 30 Mar | 170-5 v BinfieldChipstead 0-5 Binfield | Isthmian League - South Central Division |
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