| 1 | Sat 9 Aug | 32-0 v Tiverton TownTiverton Town 0-2 Chertsey Town | Southern League - Premier South |
| 2 | Tue 12 Aug | 30-1 v BerkhamstedChertsey Town 0-1 Berkhamsted | Southern League - Premier South |
| 3 | Sat 16 Aug | 30-1 v Farnham TownChertsey Town 0-1 Farnham Town | Southern League - Premier South |
| 4 | Sat 23 Aug | 30-0 v Yate TownYate Town 0-0 Chertsey Town | Southern League - Premier South |
| 5 | Mon 25 Aug | 33-3 v UxbridgeChertsey Town 3-3 Uxbridge | Southern League - Premier South |
| 6 | Sat 6 Sep | 30-1 v Poole TownPoole Town 1-0 Chertsey Town | Southern League - Premier South |
| 7 | Tue 23 Sep | 32-0 v Havant & WaterloovilleChertsey Town 2-0 Havant & Waterlooville | Southern League - Premier South |
| 8 | Sat 4 Oct | 31-2 v TilburyChertsey Town 1-2 Tilbury | Isuzu FA Trophy Third Qualifying Round |
| 9 | Tue 7 Oct | 33-3 v LeatherheadChertsey Town 3-3 Leatherhead | Surrey Senior Cup First Round |
| 10 | Sat 11 Oct | 3 2-0 v Taunton TownTaunton Town 0-2 Chertsey Town | Southern League - Premier South |
| 11 | Tue 14 Oct | 3 1-2 v Basingstoke TownBasingstoke Town 2-1 Chertsey Town | Southern League - Premier South |
| 12 | Sat 18 Oct | 3 1-1 v Bracknell TownChertsey Town 1-1 Bracknell Town | Southern League - Premier South |
| 13 | Tue 21 Oct | 31-1 v SholingChertsey Town 1-1 Sholing | Southern League - Premier South |
| 14 | Sat 1 Nov | 31-4 v Wimborne TownWimborne Town 4-1 Chertsey Town | Southern League - Premier South |
| 15 | Sat 8 Nov | 30-0 v Dorchester TownDorchester Town 0-0 Chertsey Town | Southern League - Premier South |
| 16 | Sat 15 Nov | 34-0 v Evesham UnitedChertsey Town 4-0 Evesham United | Southern League - Premier South |
| 17 | Tue 18 Nov | 3 2-1 v Hanwell TownChertsey Town 2-1 Hanwell Town | Southern League - Premier South |
| 18 | Sat 22 Nov | 3 0-2 v Gloucester CityGloucester City 2-0 Chertsey Town | Southern League - Premier South |
| 19 | Wed 26 Nov | 31-1 v Havant & WaterloovilleHavant & Waterlooville 1-1 Chertsey Town | Southern League - Premier South |
| 20 | Sat 6 Dec | 34-0 v WeymouthChertsey Town 4-0 Weymouth | Southern League - Premier South |
| 21 | Sat 13 Dec | 31-0 v Hungerford TownHungerford Town 0-1 Chertsey Town | Southern League - Premier South |
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