| 1 | Tue 29 Jul | 111-1 v Sutton Common RoversChipstead 1-1 Sutton Common Rovers | Combined Counties League Premier Division South |
| 2 | Sat 2 Aug | 110-5 v AFC WhyteleafeAFC Whyteleafe 5-0 Chipstead | Emirates FA Cup Extra Preliminary Round |
| 3 | Sat 9 Aug | 31-5 v Horley TownHorley Town 5-1 Chipstead | Combined Counties League Premier Division South |
| 4 | Sat 16 Aug | 160-2 v Camberley TownChipstead 0-2 Camberley Town | Combined Counties League Premier Division South |
| 5 | Mon 25 Aug | 23-2 v RedhillChipstead 3-2 Redhill | Combined Counties League Premier Division South |
| 6 | Sat 30 Aug | 20-3 v Fleet TownFleet Town 3-0 Chipstead | Combined Counties League Premier Division South |
| 7 | Sat 6 Sep | 21-3 v SheerwaterChipstead 1-3 Sheerwater | Combined Counties League Premier Division South |
| 8 | Sat 13 Sep | 34-3 v Badshot LeaBadshot Lea 3-4 Chipstead | Combined Counties League Premier Division South |
| 9 | Tue 16 Sep | 20-4 v Reading CityChipstead 0-4 Reading City | Cherry Red Records Premier Challenge Cup First Round |
| 10 | Sat 20 Sep | 32-3 v GreenwaysGreenways 3-2 Chipstead | Isuzu FA Vase Second Qualifying Round |
| 11 | Tue 23 Sep | 33-0 v Guildford CityChipstead 3-0 Guildford City | Combined Counties League Premier Division South |
| 12 | Fri 26 Sep | 31-3 v Epsom & EwellEpsom & Ewell 3-1 Chipstead | Combined Counties League Premier Division South |
| 13 | Sat 29 Nov | 151-4 v Guildford CityGuildford City 4-1 Chipstead | Combined Counties League Premier Division South |
| 14 | Wed 3 Dec | 72-0 v BalhamBalham 0-2 Chipstead | Combined Counties League Premier Division South |
| 15 | Sat 6 Dec | 70-2 v Tadley CallevaChipstead 0-2 Tadley Calleva | Combined Counties League Premier Division South |
| 16 | Sat 13 Dec | 100-6 v Thatcham TownThatcham Town 6-0 Chipstead | Combined Counties League Premier Division South |
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