| 1 | Sat 7 Sep | 15 1-3 v Tadley CallevaChipstead 1-3 Tadley Calleva | Combined Counties League Premier Division South |
| 2 | Tue 10 Sep | 101-1 v CobhamChipstead 1-1 Cobham | Combined Counties League Premier Division South |
| 3 | Sat 14 Sep | 104-3 v Camberley TownCamberley Town 3-4 Chipstead | Combined Counties League Premier Division South |
| 4 | Tue 8 Oct | 102-5 v RedhillChipstead 2-5 Redhill | Combined Counties League Premier Division South |
| 5 | Sat 12 Oct | 100-3 v Tooting & Mitcham UnitedTooting & Mitcham United 3-0 Chipstead | Combined Counties League Premier Division South |
| 6 | Sat 19 Oct | 122-1 v SheerwaterChipstead 2-1 Sheerwater | Combined Counties League Premier Division South |
| 7 | Sat 26 Oct | 100-2 v Jersey BullsJersey Bulls 2-0 Chipstead | Combined Counties League Premier Division South |
| 8 | Sat 9 Nov | 103-1 v BalhamChipstead 3-1 Balham | Combined Counties League Premier Division South |
| 9 | Sat 16 Nov | 100-7 v AFC WhyteleafeAFC Whyteleafe 7-0 Chipstead | Combined Counties League Premier Division South |
| 10 | Tue 19 Nov | 102-0 v Epsom & EwellChipstead 2-0 Epsom & Ewell | Combined Counties League Premier Division South |
| 11 | Tue 3 Dec | 102-0 v Horley TownHorley Town 0-2 Chipstead | Combined Counties League Premier Division South |
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