| 1 | Sat 5 Aug | 91-1 v Peacehaven & TelscombeChipstead 1-1 Peacehaven & Telscombe | Emirates FA Cup Extra Preliminary Round |
| 2 | Sat 12 Aug | 96-2 v Hartley WintneyChipstead 6-2 Hartley Wintney | Isthmian League - South Central Division |
| 3 | Sat 26 Aug | 91-1 v BinfieldBinfield 1-1 Chipstead | Isthmian League - South Central Division |
| 4 | Mon 28 Aug | 94-1 v Corinthian-CasualsChipstead 4-1 Corinthian-Casuals | Isthmian League - South Central Division |
| 5 | Sat 9 Sep | 92-4 v LancingChipstead 2-4 Lancing | Isuzu FA Trophy First Qualifying Round |
| 6 | Sat 16 Sep | 91-1 v Ashford Town (Middx)Ashford Town (Middx) 1-1 Chipstead | Isthmian League - South Central Division |
| 7 | Tue 26 Sep | 14 1-0 v LeatherheadLeatherhead 0-1 Chipstead | Velocity Cup Second Round |
| 8 | Sat 30 Sep | 90-4 v Metropolitan PoliceMetropolitan Police 4-0 Chipstead | Isthmian League - South Central Division |
| 9 | Tue 10 Oct | 174-1 v GuernseyChipstead 4-1 Guernsey | Isthmian League - South Central Division |
| 10 | Sat 14 Oct | 142-4 v Badshot LeaBadshot Lea 4-2 Chipstead | Isthmian League - South Central Division |
| 11 | Sat 21 Oct | 91-0 v Ascot UnitedChipstead 1-0 Ascot United | Isthmian League - South Central Division |
| 12 | Tue 31 Oct | 92-2 v South Park (Reigate)South Park (Reigate) 2-2 Chipstead | Velocity Cup Third Round |
| 13 | Tue 7 Nov | 9 0-4 v LeatherheadChipstead 0-4 Leatherhead | Isthmian League - South Central Division |
| 14 | Sat 11 Nov | 91-3 v NorthwoodChipstead 1-3 Northwood | Isthmian League - South Central Division |
| 15 | Sat 25 Nov | 92-3 v Sutton Common RoversChipstead 2-3 Sutton Common Rovers | Isthmian League - South Central Division |
| 16 | Sat 2 Dec | 121-2 v UxbridgeUxbridge 2-1 Chipstead | Isthmian League - South Central Division |
| 17 | Sat 16 Dec | 90-3 v Thatcham TownThatcham Town 3-0 Chipstead | Isthmian League - South Central Division |
| 18 | Sat 23 Dec | 9 1-3 v Hanworth VillaHanworth Villa 3-1 Chipstead | Isthmian League - South Central Division |
| 19 | Tue 26 Dec | 91-4 v South Park (Reigate)Chipstead 1-4 South Park (Reigate) | Isthmian League - South Central Division |
| 20 | Mon 1 Jan | 91-0 v Corinthian-CasualsCorinthian-Casuals 0-1 Chipstead | Isthmian League - South Central Division |
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