| 1 | Sat 21 Oct | 71-0 v Ascot UnitedChipstead 1-0 Ascot United | Isthmian League - South Central Division |
| 2 | Sat 28 Oct | 71-2 v Chertsey TownChertsey Town 2-1 Chipstead | Isthmian League - South Central Division |
| 3 | Tue 31 Oct | 72-2 v South Park (Reigate)South Park (Reigate) 2-2 Chipstead | Velocity Cup Third Round |
| 4 | Tue 7 Nov | 70-4 v LeatherheadChipstead 0-4 Leatherhead | Isthmian League - South Central Division |
| 5 | Sat 11 Nov | 71-3 v NorthwoodChipstead 1-3 Northwood | Isthmian League - South Central Division |
| 6 | Sat 25 Nov | 152-3 v Sutton Common RoversChipstead 2-3 Sutton Common Rovers | Isthmian League - South Central Division |
| 7 | Tue 28 Nov | 110-1 v South Park (Reigate)South Park (Reigate) 1-0 Chipstead | Surrey Senior Cup Second Round |
| 8 | Sat 2 Dec | 111-2 v UxbridgeUxbridge 2-1 Chipstead | Isthmian League - South Central Division |
| 9 | Sat 16 Dec | 110-3 v Thatcham TownThatcham Town 3-0 Chipstead | Isthmian League - South Central Division |
| 10 | Sat 23 Dec | 7 1-3 v Hanworth VillaHanworth Villa 3-1 Chipstead | Isthmian League - South Central Division |
| 11 | Tue 26 Dec | 71-4 v South Park (Reigate)Chipstead 1-4 South Park (Reigate) | Isthmian League - South Central Division |
| 12 | Mon 1 Jan | 71-0 v Corinthian-CasualsCorinthian-Casuals 0-1 Chipstead | Isthmian League - South Central Division |
| 13 | Tue 9 Jan | 70-1 v SouthallChipstead 0-1 Southall | Isthmian League - South Central Division |
| 14 | Sat 13 Jan | 72-2 v Ashford Town (Middx)Chipstead 2-2 Ashford Town (Middx) | Isthmian League - South Central Division |
| 15 | Tue 23 Jan | 71-2 v Badshot LeaBadshot Lea 2-1 Chipstead | Velocity Cup Fourth Round |
| 16 | Sat 27 Jan | 70-2 v Metropolitan PoliceChipstead 0-2 Metropolitan Police | Isthmian League - South Central Division |
| 17 | Wed 31 Jan | 73-5 v GuernseyGuernsey 5-3 Chipstead | Isthmian League - South Central Division |
| 18 | Sat 3 Feb | 70-0 v Badshot LeaChipstead 0-0 Badshot Lea | Isthmian League - South Central Division |
| 19 | Sat 16 Mar | 122-0 v UxbridgeChipstead 2-0 Uxbridge | Isthmian League - South Central Division |
| 20 | Tue 19 Mar | 120-1 v WestfieldChipstead 0-1 Westfield | Isthmian League - South Central Division |
| 21 | Sat 23 Mar | 120-2 v Sutton Common RoversSutton Common Rovers 2-0 Chipstead | Isthmian League - South Central Division |
| 22 | Sat 30 Mar | 120-5 v BinfieldChipstead 0-5 Binfield | Isthmian League - South Central Division |
| 23 | Mon 1 Apr | 161-2 v South Park (Reigate)South Park (Reigate) 2-1 Chipstead | Isthmian League - South Central Division |
| 24 | Sat 6 Apr | 112-0 v Hartley WintneyHartley Wintney 0-2 Chipstead | Isthmian League - South Central Division |
| 25 | Sat 13 Apr | 110-0 v Hanworth VillaChipstead 0-0 Hanworth Villa | Isthmian League - South Central Division |
| 26 | Sat 20 Apr | 110-3 v Thatcham TownChipstead 0-3 Thatcham Town | Isthmian League - South Central Division |
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