| 1 | Tue 29 Jul | 111-1 v Sutton Common RoversChipstead 1-1 Sutton Common Rovers | Combined Counties League Premier Division South |
| 2 | Sat 2 Aug | 110-5 v AFC WhyteleafeAFC Whyteleafe 5-0 Chipstead | Emirates FA Cup Extra Preliminary Round |
| 3 | Sat 9 Aug | 31-5 v Horley TownHorley Town 5-1 Chipstead | Combined Counties League Premier Division South |
| 4 | Sat 16 Aug | 160-2 v Camberley TownChipstead 0-2 Camberley Town | Combined Counties League Premier Division South |
| 5 | Mon 25 Aug | 23-2 v RedhillChipstead 3-2 Redhill | Combined Counties League Premier Division South |
| 6 | Sat 30 Aug | 20-3 v Fleet TownFleet Town 3-0 Chipstead | Combined Counties League Premier Division South |
| 7 | Sat 6 Sep | 21-3 v SheerwaterChipstead 1-3 Sheerwater | Combined Counties League Premier Division South |
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