| 1 | Sat 7 Sep | 15 1-3 v Tadley CallevaChipstead 1-3 Tadley Calleva | Combined Counties League Premier Division South |
| 2 | Tue 10 Sep | 101-1 v CobhamChipstead 1-1 Cobham | Combined Counties League Premier Division South |
| 3 | Sat 14 Sep | 104-3 v Camberley TownCamberley Town 3-4 Chipstead | Combined Counties League Premier Division South |
| 4 | Tue 8 Oct | 102-5 v RedhillChipstead 2-5 Redhill | Combined Counties League Premier Division South |
| 5 | Sat 12 Oct | 100-3 v Tooting & Mitcham UnitedTooting & Mitcham United 3-0 Chipstead | Combined Counties League Premier Division South |
| 6 | Sat 19 Oct | 122-1 v SheerwaterChipstead 2-1 Sheerwater | Combined Counties League Premier Division South |
| 7 | Sat 26 Oct | 100-2 v Jersey BullsJersey Bulls 2-0 Chipstead | Combined Counties League Premier Division South |
| 8 | Sat 9 Nov | 103-1 v BalhamChipstead 3-1 Balham | Combined Counties League Premier Division South |
| 9 | Sat 16 Nov | 100-7 v AFC WhyteleafeAFC Whyteleafe 7-0 Chipstead | Combined Counties League Premier Division South |
| 10 | Tue 19 Nov | 102-0 v Epsom & EwellChipstead 2-0 Epsom & Ewell | Combined Counties League Premier Division South |
| 11 | Tue 3 Dec | 102-0 v Horley TownHorley Town 0-2 Chipstead | Combined Counties League Premier Division South |
| 12 | Tue 10 Dec | 101-8 v Jersey BullsChipstead 1-8 Jersey Bulls | Combined Counties League Premier Division South |
| 13 | Tue 17 Dec | 103-2 v Corinthian-CasualsChipstead 3-2 Corinthian-Casuals | Combined Counties League Premier Division South |
| 14 | Sat 21 Dec | 101-1 v Tadley CallevaTadley Calleva 1-1 Chipstead | Combined Counties League Premier Division South |
| 15 | Sat 28 Dec | 101-4 v KnaphillChipstead 1-4 Knaphill | Combined Counties League Premier Division South |
| 16 | Sat 18 Jan | 101-6 v SheerwaterSheerwater 6-1 Chipstead | Combined Counties League Premier Division South |
| 17 | Sat 1 Feb | 102-2 v Sandhurst TownSandhurst Town 2-2 Chipstead | Combined Counties League Premier Division South |
| 18 | Sat 8 Feb | 101-2 v AltonChipstead 1-2 Alton | Combined Counties League Premier Division South |
| 19 | Sat 15 Feb | 100-4 v AFC WhyteleafeChipstead 0-4 AFC Whyteleafe | Combined Counties League Premier Division South |
| 20 | Sat 22 Feb | 151-3 v BalhamBalham 3-1 Chipstead | Combined Counties League Premier Division South |
| 21 | Tue 25 Feb | 141-2 v Camberley TownChipstead 1-2 Camberley Town | Combined Counties League Premier Division South |
| 22 | Sat 1 Mar | 12 0-2 v Fleet TownChipstead 0-2 Fleet Town | Combined Counties League Premier Division South |
| 23 | Sat 8 Mar | 120-2 v Guildford CityChipstead 0-2 Guildford City | Combined Counties League Premier Division South |
| 24 | Tue 11 Mar | 101-0 v Sandhurst TownChipstead 1-0 Sandhurst Town | Combined Counties League Premier Division South |
| 25 | Sat 15 Mar | 102-2 v Corinthian-CasualsCorinthian-Casuals 2-2 Chipstead | Combined Counties League Premier Division South |
| 26 | Tue 18 Mar | 101-2 v Tooting & Mitcham UnitedChipstead 1-2 Tooting & Mitcham United | Combined Counties League Premier Division South |
| 27 | Sat 22 Mar | 101-1 v Abbey RangersChipstead 1-1 Abbey Rangers | Combined Counties League Premier Division South |
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