| 1 | Sat 7 Sep | 53-3 v Winchester CityChertsey Town 3-3 Winchester City | Southern League - Premier South |
| 2 | Sat 14 Sep | 5 2-0 v Hanwell TownHanwell Town 0-2 Chertsey Town | Emirates FA Cup Second Qualifying Round |
| 3 | Sat 5 Oct | 5 1-1 v Billericay TownChertsey Town 1-1 Billericay Town | Isuzu FA Trophy Third Qualifying Round |
| 4 | Sat 12 Oct | 51-3 v Sutton UnitedChertsey Town 1-3 Sutton United | Emirates FA Cup Fourth Qualifying Round |
| 5 | Sat 19 Oct | 51-2 v Plymouth ParkwayChertsey Town 1-2 Plymouth Parkway | Southern League - Premier South |
| 6 | Tue 22 Oct | 54-0 v SholingChertsey Town 4-0 Sholing | Southern League - Premier South |
| 7 | Sat 26 Oct | 53-0 v UxbridgeUxbridge 0-3 Chertsey Town | Isuzu FA Trophy First Round |
| 8 | Sat 2 Nov | 53-1 v Wimborne TownWimborne Town 1-3 Chertsey Town | Southern League - Premier South |
| 9 | Sat 16 Nov | 53-2 v Bath CityBath City 2-3 Chertsey Town | Isuzu FA Trophy Second Round |
| 10 | Wed 11 Dec | 51-0 v Dagenham & RedbridgeChertsey Town 1-0 Dagenham & Redbridge | Isuzu FA Trophy Third Round |
| 11 | Thu 26 Dec | 52-1 v Hanwell TownHanwell Town 1-2 Chertsey Town | Southern League - Premier South |
| 12 | Mon 21 Apr | 50-2 v Hanwell TownChertsey Town 0-2 Hanwell Town | Southern League - Premier South |
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