| 1 | Sat 12 Aug | 16-2 v Hartley WintneyChipstead 6-2 Hartley Wintney | Isthmian League - South Central Division |
| 2 | Sat 26 Aug | 11-1 v BinfieldBinfield 1-1 Chipstead | Isthmian League - South Central Division |
| 3 | Mon 28 Aug | 14-1 v Corinthian-CasualsChipstead 4-1 Corinthian-Casuals | Isthmian League - South Central Division |
| 4 | Sat 9 Sep | 12-4 v LancingChipstead 2-4 Lancing | Isuzu FA Trophy First Qualifying Round |
| 5 | Sat 16 Sep | 11-1 v Ashford Town (Middx)Ashford Town (Middx) 1-1 Chipstead | Isthmian League - South Central Division |
| 6 | Sat 23 Sep | 11-4 v Raynes Park ValeChipstead 1-4 Raynes Park Vale | Isthmian League - South Central Division |
| 7 | Tue 26 Sep | 11-0 v LeatherheadLeatherhead 0-1 Chipstead | Velocity Cup Second Round |
| 8 | Sat 23 Dec | 11-3 v Hanworth VillaHanworth Villa 3-1 Chipstead | Isthmian League - South Central Division |
| 9 | Tue 26 Dec | 11-4 v South Park (Reigate)Chipstead 1-4 South Park (Reigate) | Isthmian League - South Central Division |
| 10 | Mon 1 Jan | 11-0 v Corinthian-CasualsCorinthian-Casuals 0-1 Chipstead | Isthmian League - South Central Division |
| 11 | Tue 9 Jan | 10-1 v SouthallChipstead 0-1 Southall | Isthmian League - South Central Division |
| 12 | Sat 13 Jan | 12-2 v Ashford Town (Middx)Chipstead 2-2 Ashford Town (Middx) | Isthmian League - South Central Division |
| 13 | Sat 23 Mar | 10-2 v Sutton Common RoversSutton Common Rovers 2-0 Chipstead | Isthmian League - South Central Division |
| 14 | Sat 30 Mar | 10-5 v BinfieldChipstead 0-5 Binfield | Isthmian League - South Central Division |
| 15 | Mon 1 Apr | 11-2 v South Park (Reigate)South Park (Reigate) 2-1 Chipstead | Isthmian League - South Central Division |
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