| 1 | Mon 28 Aug | 114-1 v Corinthian-CasualsChipstead 4-1 Corinthian-Casuals | Isthmian League - South Central Division |
| 2 | Sat 9 Sep | 112-4 v LancingChipstead 2-4 Lancing | Isuzu FA Trophy First Qualifying Round |
| 3 | Sat 16 Sep | 121-1 v Ashford Town (Middx)Ashford Town (Middx) 1-1 Chipstead | Isthmian League - South Central Division |
| 4 | Sat 23 Sep | 91-4 v Raynes Park ValeChipstead 1-4 Raynes Park Vale | Isthmian League - South Central Division |
| 5 | Tue 26 Sep | 91-0 v LeatherheadLeatherhead 0-1 Chipstead | Velocity Cup Second Round |
| 6 | Sat 30 Sep | 160-4 v Metropolitan PoliceMetropolitan Police 4-0 Chipstead | Isthmian League - South Central Division |
| 7 | Sat 7 Oct | 91-0 v NorthwoodNorthwood 0-1 Chipstead | Isthmian League - South Central Division |
| 8 | Tue 10 Oct | 94-1 v GuernseyChipstead 4-1 Guernsey | Isthmian League - South Central Division |
| 9 | Sat 14 Oct | 92-4 v Badshot LeaBadshot Lea 4-2 Chipstead | Isthmian League - South Central Division |
| 10 | Sat 28 Oct | 121-2 v Chertsey TownChertsey Town 2-1 Chipstead | Isthmian League - South Central Division |
| 11 | Sat 11 Nov | 141-3 v NorthwoodChipstead 1-3 Northwood | Isthmian League - South Central Division |
| 12 | Sat 18 Nov | 91-3 v WestfieldWestfield 3-1 Chipstead | Isthmian League - South Central Division |
| 13 | Tue 28 Nov | 90-1 v South Park (Reigate)South Park (Reigate) 1-0 Chipstead | Surrey Senior Cup Second Round |
| 14 | Sat 23 Dec | 121-3 v Hanworth VillaHanworth Villa 3-1 Chipstead | Isthmian League - South Central Division |
| 15 | Tue 26 Dec | 111-4 v South Park (Reigate)Chipstead 1-4 South Park (Reigate) | Isthmian League - South Central Division |
| 16 | Mon 1 Jan | 141-0 v Corinthian-CasualsCorinthian-Casuals 0-1 Chipstead | Isthmian League - South Central Division |
| 17 | Tue 9 Jan | 90-1 v SouthallChipstead 0-1 Southall | Isthmian League - South Central Division |
| 18 | Sat 13 Jan | 92-2 v Ashford Town (Middx)Chipstead 2-2 Ashford Town (Middx) | Isthmian League - South Central Division |
| 19 | Tue 23 Jan | 91-2 v Badshot LeaBadshot Lea 2-1 Chipstead | Velocity Cup Fourth Round |
| 20 | Sat 27 Jan | 90-2 v Metropolitan PoliceChipstead 0-2 Metropolitan Police | Isthmian League - South Central Division |
| 21 | Wed 31 Jan | 93-5 v GuernseyGuernsey 5-3 Chipstead | Isthmian League - South Central Division |
| 22 | Tue 6 Feb | 121-2 v MarlowChipstead 1-2 Marlow | Isthmian League - South Central Division |
| 23 | Sat 10 Feb | 140-1 v Ascot UnitedAscot United 1-0 Chipstead | Isthmian League - South Central Division |
| 24 | Tue 13 Feb | 91-2 v Raynes Park ValeRaynes Park Vale 2-1 Chipstead | Isthmian League - South Central Division |
| 25 | Sat 17 Feb | 91-2 v Chertsey TownChipstead 1-2 Chertsey Town | Isthmian League - South Central Division |
| 26 | Sat 16 Mar | 112-0 v UxbridgeChipstead 2-0 Uxbridge | Isthmian League - South Central Division |
| 27 | Tue 19 Mar | 110-1 v WestfieldChipstead 0-1 Westfield | Isthmian League - South Central Division |
| 28 | Sat 23 Mar | 110-2 v Sutton Common RoversSutton Common Rovers 2-0 Chipstead | Isthmian League - South Central Division |
| 29 | Mon 1 Apr | 111-2 v South Park (Reigate)South Park (Reigate) 2-1 Chipstead | Isthmian League - South Central Division |
| 30 | Sat 20 Apr | 150-3 v Thatcham TownChipstead 0-3 Thatcham Town | Isthmian League - South Central Division |
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