| 1 | Tue 8 Sep | 161-0 v Yateley UnitedYateley United 0-1 Chipstead | Combined Counties League Premier Division South |
| 2 | Sat 12 Sep | 145-2 v Seaford TownSeaford Town 2-5 Chipstead | FA Vase Second Qualifying Round |
| 3 | Sat 19 Sep | 120-0 v Badshot LeaBadshot Lea 0-0 Chipstead | Combined Counties League Premier Division South |
| 4 | Sat 26 Sep | 140-2 v Camberley TownCamberley Town 2-0 Chipstead | Combined Counties League Premier Division South |
| 5 | Sat 3 Oct | 33-0 v SheerwaterChipstead 3-0 Sheerwater | Combined Counties League Premier Division South |
| 6 | Sat 10 Oct | 31-2 v LingfieldLingfield 2-1 Chipstead | FA Vase First Round |
| 7 | Sat 17 Oct | 80-2 v BalhamChipstead 0-2 Balham | Cherry Red Records Premier Challenge Cup First Round |
| 8 | Wed 21 Oct | 81-2 v BalhamBalham 2-1 Chipstead | Combined Counties League Premier Division South |
| 9 | Sat 24 Oct | 80-2 v Tadley CallevaTadley Calleva 2-0 Chipstead | Combined Counties League Premier Division South |
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