| 1 | Sat 3 Aug | 140-2 v Athletic NewhamChipstead 0-2 Athletic Newham | Emirates FA Cup Extra Preliminary Round |
| 2 | Tue 13 Aug | 71-0 v Spelthorne SportsSpelthorne Sports 0-1 Chipstead | Combined Counties League Premier Division South |
| 3 | Sat 17 Aug | 142-5 v Horley TownChipstead 2-5 Horley Town | Combined Counties League Premier Division South |
| 4 | Sat 24 Aug | 143-1 v Chessington & Hook UnitedChipstead 3-1 Chessington & Hook United | Isuzu FA Vase First Qualifying Round |
| 5 | Mon 26 Aug | 140-5 v RedhillRedhill 5-0 Chipstead | Combined Counties League Premier Division South |
| 6 | Sat 31 Aug | 143-2 v Guildford CityGuildford City 2-3 Chipstead | Combined Counties League Premier Division South |
| 7 | Tue 3 Sep | 140-2 v Epsom & EwellEpsom & Ewell 2-0 Chipstead | Combined Counties League Premier Division South |
| 8 | Sat 7 Sep | 141-3 v Tadley CallevaChipstead 1-3 Tadley Calleva | Combined Counties League Premier Division South |
| 9 | Tue 10 Sep | 141-1 v CobhamChipstead 1-1 Cobham | Combined Counties League Premier Division South |
| 10 | Sat 14 Sep | 144-3 v Camberley TownCamberley Town 3-4 Chipstead | Combined Counties League Premier Division South |
| 11 | Sat 21 Sep | 140-3 v VCD AthleticChipstead 0-3 VCD Athletic | Isuzu FA Vase Second Qualifying Round |
| 12 | Wed 25 Sep | 141-1 v BurnhamBurnham 1-1 Chipstead | Cherry Red Records Premier Challenge Cup First Round |
| 13 | Sat 5 Oct | 141-3 v Fleet TownFleet Town 3-1 Chipstead | Combined Counties League Premier Division South |
| 14 | Tue 8 Oct | 142-5 v RedhillChipstead 2-5 Redhill | Combined Counties League Premier Division South |
| 15 | Sat 12 Oct | 2 0-3 v Tooting & Mitcham UnitedTooting & Mitcham United 3-0 Chipstead | Combined Counties League Premier Division South |
| 16 | Sat 19 Oct | 14 2-1 v SheerwaterChipstead 2-1 Sheerwater | Combined Counties League Premier Division South |
| 17 | Sat 26 Oct | 140-2 v Jersey BullsJersey Bulls 2-0 Chipstead | Combined Counties League Premier Division South |
| 18 | Sat 2 Nov | 111-4 v CobhamCobham 4-1 Chipstead | Combined Counties League Premier Division South |
| 19 | Sat 9 Nov | 143-1 v BalhamChipstead 3-1 Balham | Combined Counties League Premier Division South |
| 20 | Sat 16 Nov | 140-7 v AFC WhyteleafeAFC Whyteleafe 7-0 Chipstead | Combined Counties League Premier Division South |
| 21 | Tue 19 Nov | 142-0 v Epsom & EwellChipstead 2-0 Epsom & Ewell | Combined Counties League Premier Division South |
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