| 1 | Sat 3 Aug | 120-2 v Athletic NewhamChipstead 0-2 Athletic Newham | Emirates FA Cup Extra Preliminary Round |
| 2 | Sat 10 Aug | 22-3 v KnaphillKnaphill 3-2 Chipstead | Combined Counties League Premier Division South |
| 3 | Tue 13 Aug | 21-0 v Spelthorne SportsSpelthorne Sports 0-1 Chipstead | Combined Counties League Premier Division South |
| 4 | Sat 17 Aug | 22-5 v Horley TownChipstead 2-5 Horley Town | Combined Counties League Premier Division South |
| 5 | Sat 24 Aug | 23-1 v Chessington & Hook UnitedChipstead 3-1 Chessington & Hook United | Isuzu FA Vase First Qualifying Round |
| 6 | Mon 26 Aug | 2 0-5 v RedhillRedhill 5-0 Chipstead | Combined Counties League Premier Division South |
| 7 | Tue 10 Sep | 21-1 v CobhamChipstead 1-1 Cobham | Combined Counties League Premier Division South |
| 8 | Sat 14 Sep | 24-3 v Camberley TownCamberley Town 3-4 Chipstead | Combined Counties League Premier Division South |
| 9 | Sat 21 Sep | 20-3 v VCD AthleticChipstead 0-3 VCD Athletic | Isuzu FA Vase Second Qualifying Round |
| 10 | Sat 5 Oct | 21-3 v Fleet TownFleet Town 3-1 Chipstead | Combined Counties League Premier Division South |
| 11 | Sat 19 Oct | 17 2-1 v SheerwaterChipstead 2-1 Sheerwater | Combined Counties League Premier Division South |
| 12 | Sat 26 Oct | 70-2 v Jersey BullsJersey Bulls 2-0 Chipstead | Combined Counties League Premier Division South |
| 13 | Sat 2 Nov | 71-4 v CobhamCobham 4-1 Chipstead | Combined Counties League Premier Division South |
| 14 | Sat 9 Nov | 23-1 v BalhamChipstead 3-1 Balham | Combined Counties League Premier Division South |
| 15 | Sat 16 Nov | 90-7 v AFC WhyteleafeAFC Whyteleafe 7-0 Chipstead | Combined Counties League Premier Division South |
| 16 | Tue 19 Nov | 22-0 v Epsom & EwellChipstead 2-0 Epsom & Ewell | Combined Counties League Premier Division South |
| 17 | Tue 3 Dec | 22-0 v Horley TownHorley Town 0-2 Chipstead | Combined Counties League Premier Division South |
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