| 1 | Sat 3 Aug | 50-2 v Athletic NewhamChipstead 0-2 Athletic Newham | Emirates FA Cup Extra Preliminary Round |
| 2 | Sat 10 Aug | 6 2-3 v KnaphillKnaphill 3-2 Chipstead | Combined Counties League Premier Division South |
| 3 | Tue 13 Aug | 51-0 v Spelthorne SportsSpelthorne Sports 0-1 Chipstead | Combined Counties League Premier Division South |
| 4 | Sat 17 Aug | 52-5 v Horley TownChipstead 2-5 Horley Town | Combined Counties League Premier Division South |
| 5 | Sat 31 Aug | 53-2 v Guildford CityGuildford City 2-3 Chipstead | Combined Counties League Premier Division South |
| 6 | Tue 3 Sep | 50-2 v Epsom & EwellEpsom & Ewell 2-0 Chipstead | Combined Counties League Premier Division South |
| 7 | Sat 7 Sep | 51-3 v Tadley CallevaChipstead 1-3 Tadley Calleva | Combined Counties League Premier Division South |
| 8 | Tue 10 Sep | 51-1 v CobhamChipstead 1-1 Cobham | Combined Counties League Premier Division South |
| 9 | Sat 14 Sep | 54-3 v Camberley TownCamberley Town 3-4 Chipstead | Combined Counties League Premier Division South |
| 10 | Sat 21 Sep | 5 0-3 v VCD AthleticChipstead 0-3 VCD Athletic | Isuzu FA Vase Second Qualifying Round |
| 11 | Wed 25 Sep | 51-1 v BurnhamBurnham 1-1 Chipstead | Cherry Red Records Premier Challenge Cup First Round |
| 12 | Sat 12 Oct | 60-3 v Tooting & Mitcham UnitedTooting & Mitcham United 3-0 Chipstead | Combined Counties League Premier Division South |
| 13 | Sat 26 Oct | 50-2 v Jersey BullsJersey Bulls 2-0 Chipstead | Combined Counties League Premier Division South |
| 14 | Sat 2 Nov | 51-4 v CobhamCobham 4-1 Chipstead | Combined Counties League Premier Division South |
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