| 1 | Sat 9 Aug | 22-0 v Tiverton TownTiverton Town 0-2 Chertsey Town | Southern League - Premier South |
| 2 | Tue 12 Aug | 2 0-1 v BerkhamstedChertsey Town 0-1 Berkhamsted | Southern League - Premier South |
| 3 | Sat 16 Aug | 20-1 v Farnham TownChertsey Town 0-1 Farnham Town | Southern League - Premier South |
| 4 | Sat 23 Aug | 2 0-0 v Yate TownYate Town 0-0 Chertsey Town | Southern League - Premier South |
| 5 | Mon 25 Aug | 23-3 v UxbridgeChertsey Town 3-3 Uxbridge | Southern League - Premier South |
| 6 | Sat 6 Sep | 20-1 v Poole TownPoole Town 1-0 Chertsey Town | Southern League - Premier South |
| 7 | Tue 9 Sep | 22-1 v Hanwell TownHanwell Town 1-2 Chertsey Town | Southern League - Premier South |
| 8 | Tue 23 Sep | 22-0 v Havant & WaterloovilleChertsey Town 2-0 Havant & Waterlooville | Southern League - Premier South |
| 9 | Sat 4 Oct | 21-2 v TilburyChertsey Town 1-2 Tilbury | Isuzu FA Trophy Third Qualifying Round |
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