| 1 | Sat 8 Aug | 21-0 v Gloucester CityGloucester City 0-1 Chertsey Town | Southern League - Premier South |
| 2 | Tue 11 Aug | 24-1 v BerkhamstedChertsey Town 4-1 Berkhamsted | Southern League - Premier South |
| 3 | Sat 15 Aug | 21-1 v Yate TownChertsey Town 1-1 Yate Town | Southern League - Premier South |
| 4 | Sat 22 Aug | 24-2 v SholingSholing 2-4 Chertsey Town | Southern League - Premier South |
| 5 | Sat 29 Aug | 2 1-2 v Frome TownChertsey Town 1-2 Frome Town | Southern League - Premier South |
| 6 | Mon 31 Aug | 21-4 v Hanworth VillaHanworth Villa 4-1 Chertsey Town | Southern League - Premier South |
| 7 | Sat 5 Sep | 21-1 v Carshalton AthleticChertsey Town 1-1 Carshalton Athletic | Emirates FA Cup First Qualifying Round |
| 8 | Mon 7 Sep | 22-1 v Carshalton AthleticCarshalton Athletic 1-2 Chertsey Town | Emirates FA Cup First Qualifying Round Replay |
| 9 | Sat 12 Sep | 2 5-0 v Malvern TownChertsey Town 5-0 Malvern Town | Southern League - Premier South |
| 10 | Sat 19 Sep | 23-2 v AFC Greenwich BoroughChertsey Town 3-2 AFC Greenwich Borough | Emirates FA Cup Second Qualifying Round |
| 11 | Tue 22 Sep | 2 2-2 v Chichester CityChichester City 2-2 Chertsey Town | Southern League - Premier South |
| 12 | Tue 29 Sep | 21-3 v Poole TownChertsey Town 1-3 Poole Town | Southern League - Premier South |
| 13 | Sat 3 Oct | 22-0 v Sheppey UnitedSheppey United 0-2 Chertsey Town | Emirates FA Cup Third Qualifying Round |
| 14 | Sat 10 Oct | 22-2 v Chippenham TownChertsey Town 2-2 Chippenham Town | Southern League - Premier South |
| 15 | Tue 13 Oct | 21-1 v Hanwell TownHanwell Town 1-1 Chertsey Town | Southern League - Premier South |
| 16 | Tue 20 Oct | 2 2-0 v Evesham UnitedChertsey Town 2-0 Evesham United | Southern League - Premier South |
| 17 | Sat 24 Oct | 24-0 v TakeleyTakeley 0-4 Chertsey Town | FA Trophy First Round |
| 18 | Tue 27 Oct | 22-2 v Poole TownPoole Town 2-2 Chertsey Town | Southern League - Premier South |
| 19 | Sat 31 Oct | 24-3 v Basingstoke TownChertsey Town 4-3 Basingstoke Town | Southern League - Premier South |
| 20 | Tue 3 Nov | 22-1 v Bracknell TownBracknell Town 1-2 Chertsey Town | Southern League - Premier South |
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