| 1 | Sat 8 Aug | 201-0 v Gloucester CityGloucester City 0-1 Chertsey Town | Southern League - Premier South |
| 2 | Tue 11 Aug | 20 4-1 v BerkhamstedChertsey Town 4-1 Berkhamsted | Southern League - Premier South |
| 3 | Sat 15 Aug | 201-1 v Yate TownChertsey Town 1-1 Yate Town | Southern League - Premier South |
| 4 | Sat 22 Aug | 20 4-2 v SholingSholing 2-4 Chertsey Town | Southern League - Premier South |
| 5 | Sat 29 Aug | 201-2 v Frome TownChertsey Town 1-2 Frome Town | Southern League - Premier South |
| 6 | Mon 31 Aug | 201-4 v Hanworth VillaHanworth Villa 4-1 Chertsey Town | Southern League - Premier South |
| 7 | Sat 5 Sep | 20 1-1 v Carshalton AthleticChertsey Town 1-1 Carshalton Athletic | Emirates FA Cup First Qualifying Round |
| 8 | Mon 7 Sep | 202-1 v Carshalton AthleticCarshalton Athletic 1-2 Chertsey Town | Emirates FA Cup First Qualifying Round Replay |
| 9 | Tue 29 Sep | 201-3 v Poole TownChertsey Town 1-3 Poole Town | Southern League - Premier South |
| 10 | Sat 3 Oct | 202-0 v Sheppey UnitedSheppey United 0-2 Chertsey Town | Emirates FA Cup Third Qualifying Round |
| 11 | Sat 10 Oct | 202-2 v Chippenham TownChertsey Town 2-2 Chippenham Town | Southern League - Premier South |
| 12 | Tue 13 Oct | 201-1 v Hanwell TownHanwell Town 1-1 Chertsey Town | Southern League - Premier South |
| 13 | Sat 17 Oct | 20 0-2 v Plymouth ParkwayPlymouth Parkway 2-0 Chertsey Town | Emirates FA Cup Fourth Qualifying Round |
| 14 | Tue 20 Oct | 202-0 v Evesham UnitedChertsey Town 2-0 Evesham United | Southern League - Premier South |
| 15 | Sat 24 Oct | 204-0 v TakeleyTakeley 0-4 Chertsey Town | FA Trophy First Round |
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