| 1 | Sat 3 Aug | 150-2 v Athletic NewhamChipstead 0-2 Athletic Newham | Emirates FA Cup Extra Preliminary Round |
| 2 | Tue 13 Aug | 141-0 v Spelthorne SportsSpelthorne Sports 0-1 Chipstead | Combined Counties League Premier Division South |
| 3 | Sat 17 Aug | 162-5 v Horley TownChipstead 2-5 Horley Town | Combined Counties League Premier Division South |
| 4 | Sat 24 Aug | 5 3-1 v Chessington & Hook UnitedChipstead 3-1 Chessington & Hook United | Isuzu FA Vase First Qualifying Round |
| 5 | Mon 26 Aug | 50-5 v RedhillRedhill 5-0 Chipstead | Combined Counties League Premier Division South |
| 6 | Sat 31 Aug | 83-2 v Guildford CityGuildford City 2-3 Chipstead | Combined Counties League Premier Division South |
| 7 | Tue 3 Sep | 80-2 v Epsom & EwellEpsom & Ewell 2-0 Chipstead | Combined Counties League Premier Division South |
| 8 | Sat 7 Sep | 81-3 v Tadley CallevaChipstead 1-3 Tadley Calleva | Combined Counties League Premier Division South |
| 9 | Tue 10 Sep | 81-1 v CobhamChipstead 1-1 Cobham | Combined Counties League Premier Division South |
| 10 | Sat 14 Sep | 84-3 v Camberley TownCamberley Town 3-4 Chipstead | Combined Counties League Premier Division South |
| 11 | Sat 21 Sep | 80-3 v VCD AthleticChipstead 0-3 VCD Athletic | Isuzu FA Vase Second Qualifying Round |
| 12 | Sat 5 Oct | 81-3 v Fleet TownFleet Town 3-1 Chipstead | Combined Counties League Premier Division South |
| 13 | Sat 19 Oct | 82-1 v SheerwaterChipstead 2-1 Sheerwater | Combined Counties League Premier Division South |
| 14 | Sat 26 Oct | 80-2 v Jersey BullsJersey Bulls 2-0 Chipstead | Combined Counties League Premier Division South |
| 15 | Sat 2 Nov | 91-4 v CobhamCobham 4-1 Chipstead | Combined Counties League Premier Division South |
| 16 | Sat 9 Nov | 8 3-1 v BalhamChipstead 3-1 Balham | Combined Counties League Premier Division South |
| 17 | Sat 16 Nov | 80-7 v AFC WhyteleafeAFC Whyteleafe 7-0 Chipstead | Combined Counties League Premier Division South |
| 18 | Tue 3 Dec | 8 2-0 v Horley TownHorley Town 0-2 Chipstead | Combined Counties League Premier Division South |
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