| 1 | Sat 26 Aug | 14 1-1 v BinfieldBinfield 1-1 Chipstead | Isthmian League - South Central Division |
| 2 | Mon 28 Aug | 64-1 v Corinthian-CasualsChipstead 4-1 Corinthian-Casuals | Isthmian League - South Central Division |
| 3 | Sat 16 Sep | 61-1 v Ashford Town (Middx)Ashford Town (Middx) 1-1 Chipstead | Isthmian League - South Central Division |
| 4 | Sat 23 Sep | 161-4 v Raynes Park ValeChipstead 1-4 Raynes Park Vale | Isthmian League - South Central Division |
| 5 | Tue 26 Sep | 61-0 v LeatherheadLeatherhead 0-1 Chipstead | Velocity Cup Second Round |
| 6 | Sat 30 Sep | 60-4 v Metropolitan PoliceMetropolitan Police 4-0 Chipstead | Isthmian League - South Central Division |
| 7 | Tue 31 Oct | 32-2 v South Park (Reigate)South Park (Reigate) 2-2 Chipstead | Velocity Cup Third Round |
| 8 | Sat 18 Nov | 111-3 v WestfieldWestfield 3-1 Chipstead | Isthmian League - South Central Division |
| 9 | Sat 25 Nov | 42-3 v Sutton Common RoversChipstead 2-3 Sutton Common Rovers | Isthmian League - South Central Division |
| 10 | Tue 28 Nov | 30-1 v South Park (Reigate)South Park (Reigate) 1-0 Chipstead | Surrey Senior Cup Second Round |
| 11 | Sat 16 Dec | 4 0-3 v Thatcham TownThatcham Town 3-0 Chipstead | Isthmian League - South Central Division |
| 12 | Mon 1 Jan | 4 1-0 v Corinthian-CasualsCorinthian-Casuals 0-1 Chipstead | Isthmian League - South Central Division |
| 13 | Tue 9 Jan | 40-1 v SouthallChipstead 0-1 Southall | Isthmian League - South Central Division |
| 14 | Sat 13 Jan | 42-2 v Ashford Town (Middx)Chipstead 2-2 Ashford Town (Middx) | Isthmian League - South Central Division |
| 15 | Tue 23 Jan | 61-2 v Badshot LeaBadshot Lea 2-1 Chipstead | Velocity Cup Fourth Round |
| 16 | Sat 27 Jan | 60-2 v Metropolitan PoliceChipstead 0-2 Metropolitan Police | Isthmian League - South Central Division |
| 17 | Wed 31 Jan | 6 3-5 v GuernseyGuernsey 5-3 Chipstead | Isthmian League - South Central Division |
| 18 | Sat 3 Feb | 30-0 v Badshot LeaChipstead 0-0 Badshot Lea | Isthmian League - South Central Division |
| 19 | Tue 6 Feb | 6 1-2 v MarlowChipstead 1-2 Marlow | Isthmian League - South Central Division |
| 20 | Sat 30 Mar | 40-5 v BinfieldChipstead 0-5 Binfield | Isthmian League - South Central Division |
| 21 | Mon 1 Apr | 41-2 v South Park (Reigate)South Park (Reigate) 2-1 Chipstead | Isthmian League - South Central Division |
| 22 | Sat 6 Apr | 32-0 v Hartley WintneyHartley Wintney 0-2 Chipstead | Isthmian League - South Central Division |
| 23 | Sat 13 Apr | 30-0 v Hanworth VillaChipstead 0-0 Hanworth Villa | Isthmian League - South Central Division |
| 24 | Sat 20 Apr | 60-3 v Thatcham TownChipstead 0-3 Thatcham Town | Isthmian League - South Central Division |
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