| 1 | Tue 16 Sep | 90-4 v Reading CityChipstead 0-4 Reading City | Cherry Red Records Premier Challenge Cup First Round |
| 2 | Sat 20 Sep | 72-3 v GreenwaysGreenways 3-2 Chipstead | Isuzu FA Vase Second Qualifying Round |
| 3 | Tue 23 Sep | 103-0 v Guildford CityChipstead 3-0 Guildford City | Combined Counties League Premier Division South |
| 4 | Fri 26 Sep | 10 1-3 v Epsom & EwellEpsom & Ewell 3-1 Chipstead | Combined Counties League Premier Division South |
| 5 | Sat 4 Oct | 100-5 v CobhamChipstead 0-5 Cobham | Combined Counties League Premier Division South |
| 6 | Sat 11 Oct | 76-0 v Corinthian-CasualsChipstead 6-0 Corinthian-Casuals | Combined Counties League Premier Division South |
| 7 | Tue 21 Oct | 102-1 v Camberley TownChipstead 2-1 Camberley Town | Surrey Senior Cup First Round |
| 8 | Sat 25 Oct | 10 3-2 v AltonAlton 2-3 Chipstead | Combined Counties League Premier Division South |
| 9 | Sat 1 Nov | 102-1 v Abbey RangersChipstead 2-1 Abbey Rangers | Combined Counties League Premier Division South |
| 10 | Tue 4 Nov | 101-1 v Tooting & Mitcham UnitedChipstead 1-1 Tooting & Mitcham United | Combined Counties League Premier Division South |
| 11 | Sat 8 Nov | 100-1 v KnaphillKnaphill 1-0 Chipstead | Combined Counties League Premier Division South |
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