| 1 | Sat 1 Aug | 4 1-2 v Abbey RangersChipstead 1-2 Abbey Rangers | Combined Counties League Premier Division South |
| 2 | Tue 4 Aug | 4 1-2 v KnaphillKnaphill 2-1 Chipstead | Combined Counties League Premier Division South |
| 3 | Sat 22 Aug | 5 0-1 v AltonChipstead 0-1 Alton | Combined Counties League Premier Division South |
| 4 | Sat 29 Aug | 54-2 v Virginia WaterChipstead 4-2 Virginia Water | Combined Counties League Premier Division South |
| 5 | Mon 31 Aug | 50-0 v RedhillChipstead 0-0 Redhill | Combined Counties League Premier Division South |
| 6 | Tue 8 Sep | 5 1-0 v Yateley UnitedYateley United 0-1 Chipstead | Combined Counties League Premier Division South |
| 7 | Sat 12 Sep | 55-2 v Seaford TownSeaford Town 2-5 Chipstead | FA Vase Second Qualifying Round |
| 8 | Tue 15 Sep | 51-0 v Corinthian-CasualsChipstead 1-0 Corinthian-Casuals | Combined Counties League Premier Division South |
| 9 | Sat 19 Sep | 50-0 v Badshot LeaBadshot Lea 0-0 Chipstead | Combined Counties League Premier Division South |
| 10 | Sat 3 Oct | 53-0 v SheerwaterChipstead 3-0 Sheerwater | Combined Counties League Premier Division South |
| 11 | Tue 6 Oct | 51-2 v Badshot LeaChipstead 1-2 Badshot Lea | Surrey Senior Cup Preliminary Round |
| 12 | Sat 10 Oct | 51-2 v LingfieldLingfield 2-1 Chipstead | FA Vase First Round |
| 13 | Sat 17 Oct | 50-2 v BalhamChipstead 0-2 Balham | Cherry Red Records Premier Challenge Cup First Round |
| 14 | Wed 21 Oct | 51-2 v BalhamBalham 2-1 Chipstead | Combined Counties League Premier Division South |
| 15 | Sat 24 Oct | 50-2 v Tadley CallevaTadley Calleva 2-0 Chipstead | Combined Counties League Premier Division South |
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