| 1 | Sat 5 Aug | 111-1 v Peacehaven & TelscombeChipstead 1-1 Peacehaven & Telscombe | Emirates FA Cup Extra Preliminary Round |
| 2 | Tue 8 Aug | 91-4 v Peacehaven & TelscombePeacehaven & Telscombe 4-1 Chipstead | Emirates FA Cup Extra Preliminary Round Replay |
| 3 | Sat 12 Aug | 116-2 v Hartley WintneyChipstead 6-2 Hartley Wintney | Isthmian League - South Central Division |
| 4 | Sat 26 Aug | 111-1 v BinfieldBinfield 1-1 Chipstead | Isthmian League - South Central Division |
| 5 | Sat 9 Sep | 162-4 v LancingChipstead 2-4 Lancing | Isuzu FA Trophy First Qualifying Round |
| 6 | Sat 16 Sep | 111-1 v Ashford Town (Middx)Ashford Town (Middx) 1-1 Chipstead | Isthmian League - South Central Division |
| 7 | Sat 23 Sep | 111-4 v Raynes Park ValeChipstead 1-4 Raynes Park Vale | Isthmian League - South Central Division |
| 8 | Tue 26 Sep | 111-0 v LeatherheadLeatherhead 0-1 Chipstead | Velocity Cup Second Round |
| 9 | Sat 30 Sep | 110-4 v Metropolitan PoliceMetropolitan Police 4-0 Chipstead | Isthmian League - South Central Division |
| 10 | Sat 7 Oct | 151-0 v NorthwoodNorthwood 0-1 Chipstead | Isthmian League - South Central Division |
| 11 | Sat 14 Oct | 122-4 v Badshot LeaBadshot Lea 4-2 Chipstead | Isthmian League - South Central Division |
| 12 | Sat 21 Oct | 111-0 v Ascot UnitedChipstead 1-0 Ascot United | Isthmian League - South Central Division |
| 13 | Sat 28 Oct | 91-2 v Chertsey TownChertsey Town 2-1 Chipstead | Isthmian League - South Central Division |
| 14 | Tue 31 Oct | 142-2 v South Park (Reigate)South Park (Reigate) 2-2 Chipstead | Velocity Cup Third Round |
| 15 | Tue 7 Nov | 110-4 v LeatherheadChipstead 0-4 Leatherhead | Isthmian League - South Central Division |
| 16 | Sat 11 Nov | 111-3 v NorthwoodChipstead 1-3 Northwood | Isthmian League - South Central Division |
| 17 | Sat 18 Nov | 71-3 v WestfieldWestfield 3-1 Chipstead | Isthmian League - South Central Division |
| 18 | Sat 25 Nov | 112-3 v Sutton Common RoversChipstead 2-3 Sutton Common Rovers | Isthmian League - South Central Division |
| 19 | Tue 28 Nov | 70-1 v South Park (Reigate)South Park (Reigate) 1-0 Chipstead | Surrey Senior Cup Second Round |
| 20 | Sat 2 Dec | 91-2 v UxbridgeUxbridge 2-1 Chipstead | Isthmian League - South Central Division |
| 21 | Sat 16 Dec | 160-3 v Thatcham TownThatcham Town 3-0 Chipstead | Isthmian League - South Central Division |
| 22 | Sat 23 Dec | 111-3 v Hanworth VillaHanworth Villa 3-1 Chipstead | Isthmian League - South Central Division |
| 23 | Tue 26 Dec | 161-4 v South Park (Reigate)Chipstead 1-4 South Park (Reigate) | Isthmian League - South Central Division |
| 24 | Mon 1 Jan | 111-0 v Corinthian-CasualsCorinthian-Casuals 0-1 Chipstead | Isthmian League - South Central Division |
| 25 | Tue 9 Jan | 110-1 v SouthallChipstead 0-1 Southall | Isthmian League - South Central Division |
| 26 | Wed 31 Jan | 153-5 v GuernseyGuernsey 5-3 Chipstead | Isthmian League - South Central Division |
| 27 | Sat 3 Feb | 110-0 v Badshot LeaChipstead 0-0 Badshot Lea | Isthmian League - South Central Division |
| 28 | Tue 6 Feb | 111-2 v MarlowChipstead 1-2 Marlow | Isthmian League - South Central Division |
| 29 | Sat 10 Feb | 70-1 v Ascot UnitedAscot United 1-0 Chipstead | Isthmian League - South Central Division |
| 30 | Tue 13 Feb | 111-2 v Raynes Park ValeRaynes Park Vale 2-1 Chipstead | Isthmian League - South Central Division |
| 31 | Sat 17 Feb | 111-2 v Chertsey TownChipstead 1-2 Chertsey Town | Isthmian League - South Central Division |
| 32 | Sat 24 Feb | 11 0-4 v MarlowMarlow 4-0 Chipstead | Isthmian League - South Central Division |
| 33 | Tue 27 Feb | 111-1 v LeatherheadLeatherhead 1-1 Chipstead | Isthmian League - South Central Division |
| 34 | Sat 16 Mar | 72-0 v UxbridgeChipstead 2-0 Uxbridge | Isthmian League - South Central Division |
| 35 | Tue 19 Mar | 70-1 v WestfieldChipstead 0-1 Westfield | Isthmian League - South Central Division |
| 36 | Sat 23 Mar | 70-2 v Sutton Common RoversSutton Common Rovers 2-0 Chipstead | Isthmian League - South Central Division |
| 37 | Sat 30 Mar | 110-5 v BinfieldChipstead 0-5 Binfield | Isthmian League - South Central Division |
| 38 | Mon 1 Apr | 81-2 v South Park (Reigate)South Park (Reigate) 2-1 Chipstead | Isthmian League - South Central Division |
| 39 | Sat 6 Apr | 92-0 v Hartley WintneyHartley Wintney 0-2 Chipstead | Isthmian League - South Central Division |
| 40 | Sat 13 Apr | 90-0 v Hanworth VillaChipstead 0-0 Hanworth Villa | Isthmian League - South Central Division |
| 41 | Sat 20 Apr | 90-3 v Thatcham TownChipstead 0-3 Thatcham Town | Isthmian League - South Central Division |
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