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