| 1 | Sat 3 Aug | 20-2 v Athletic NewhamChipstead 0-2 Athletic Newham | Emirates FA Cup Extra Preliminary Round |
| 2 | Sat 10 Aug | 52-3 v KnaphillKnaphill 3-2 Chipstead | Combined Counties League Premier Division South |
| 3 | Tue 13 Aug | 61-0 v Spelthorne SportsSpelthorne Sports 0-1 Chipstead | Combined Counties League Premier Division South |
| 4 | Sat 17 Aug | 62-5 v Horley TownChipstead 2-5 Horley Town | Combined Counties League Premier Division South |
| 5 | Sat 7 Sep | 21-3 v Tadley CallevaChipstead 1-3 Tadley Calleva | Combined Counties League Premier Division South |
| 6 | Sat 14 Sep | 64-3 v Camberley TownCamberley Town 3-4 Chipstead | Combined Counties League Premier Division South |
| 7 | Wed 25 Sep | 31-1 v BurnhamBurnham 1-1 Chipstead | Cherry Red Records Premier Challenge Cup First Round |
| 8 | Sat 19 Oct | 22-1 v SheerwaterChipstead 2-1 Sheerwater | Combined Counties League Premier Division South |
| 9 | Sat 26 Oct | 20-2 v Jersey BullsJersey Bulls 2-0 Chipstead | Combined Counties League Premier Division South |
| 10 | Sat 2 Nov | 21-4 v CobhamCobham 4-1 Chipstead | Combined Counties League Premier Division South |
| 11 | Sat 9 Nov | 53-1 v BalhamChipstead 3-1 Balham | Combined Counties League Premier Division South |
| 12 | Sat 16 Nov | 50-7 v AFC WhyteleafeAFC Whyteleafe 7-0 Chipstead | Combined Counties League Premier Division South |
| 13 | Tue 19 Nov | 52-0 v Epsom & EwellChipstead 2-0 Epsom & Ewell | Combined Counties League Premier Division South |
| 14 | Tue 3 Dec | 42-0 v Horley TownHorley Town 0-2 Chipstead | Combined Counties League Premier Division South |
| 15 | Tue 10 Dec | 41-8 v Jersey BullsChipstead 1-8 Jersey Bulls | Combined Counties League Premier Division South |
| 16 | Tue 17 Dec | 43-2 v Corinthian-CasualsChipstead 3-2 Corinthian-Casuals | Combined Counties League Premier Division South |
| 17 | Sat 21 Dec | 41-1 v Tadley CallevaTadley Calleva 1-1 Chipstead | Combined Counties League Premier Division South |
| 18 | Sat 28 Dec | 41-4 v KnaphillChipstead 1-4 Knaphill | Combined Counties League Premier Division South |
| 19 | Sat 18 Jan | 4 1-6 v SheerwaterSheerwater 6-1 Chipstead | Combined Counties League Premier Division South |
| 20 | Sat 1 Feb | 42-2 v Sandhurst TownSandhurst Town 2-2 Chipstead | Combined Counties League Premier Division South |
| 21 | Sat 8 Feb | 51-2 v AltonChipstead 1-2 Alton | Combined Counties League Premier Division South |
| 22 | Sat 15 Feb | 50-4 v AFC WhyteleafeChipstead 0-4 AFC Whyteleafe | Combined Counties League Premier Division South |
| 23 | Sat 22 Feb | 51-3 v BalhamBalham 3-1 Chipstead | Combined Counties League Premier Division South |
| 24 | Tue 25 Feb | 51-2 v Camberley TownChipstead 1-2 Camberley Town | Combined Counties League Premier Division South |
| 25 | Sat 1 Mar | 60-2 v Fleet TownChipstead 0-2 Fleet Town | Combined Counties League Premier Division South |
| 26 | Tue 18 Mar | 41-2 v Tooting & Mitcham UnitedChipstead 1-2 Tooting & Mitcham United | Combined Counties League Premier Division South |
| 27 | Sat 22 Mar | 61-1 v Abbey RangersChipstead 1-1 Abbey Rangers | Combined Counties League Premier Division South |
| 28 | Sat 5 Apr | 53-3 v Spelthorne SportsChipstead 3-3 Spelthorne Sports | Combined Counties League Premier Division South |
| 29 | Sat 19 Apr | 52-1 v Abbey RangersAbbey Rangers 1-2 Chipstead | Combined Counties League Premier Division South |
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