| 1 | Sat 15 Aug | 211-1 v Yate TownChertsey Town 1-1 Yate Town | Southern League - Premier South |
| 2 | Sat 22 Aug | 214-2 v SholingSholing 2-4 Chertsey Town | Southern League - Premier South |
| 3 | Sat 29 Aug | 21 1-2 v Frome TownChertsey Town 1-2 Frome Town | Southern League - Premier South |
| 4 | Mon 31 Aug | 21 1-4 v Hanworth VillaHanworth Villa 4-1 Chertsey Town | Southern League - Premier South |
| 5 | Sat 5 Sep | 211-1 v Carshalton AthleticChertsey Town 1-1 Carshalton Athletic | Emirates FA Cup First Qualifying Round |
| 6 | Mon 7 Sep | 212-1 v Carshalton AthleticCarshalton Athletic 1-2 Chertsey Town | Emirates FA Cup First Qualifying Round Replay |
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