| 1 | Tue 7 Oct | 243-3 v LeatherheadChertsey Town 3-3 Leatherhead | Surrey Senior Cup First Round |
| 2 | Sat 11 Oct | 72-0 v Taunton TownTaunton Town 0-2 Chertsey Town | Southern League - Premier South |
| 3 | Tue 14 Oct | 71-2 v Basingstoke TownBasingstoke Town 2-1 Chertsey Town | Southern League - Premier South |
| 4 | Sat 18 Oct | 71-1 v Bracknell TownChertsey Town 1-1 Bracknell Town | Southern League - Premier South |
| 5 | Tue 21 Oct | 71-1 v SholingChertsey Town 1-1 Sholing | Southern League - Premier South |
| 6 | Sat 29 Nov | 251-0 v Plymouth ParkwayChertsey Town 1-0 Plymouth Parkway | Southern League - Premier South |
| 7 | Sat 6 Dec | 25 4-0 v WeymouthChertsey Town 4-0 Weymouth | Southern League - Premier South |
| 8 | Sat 13 Dec | 25 1-0 v Hungerford TownHungerford Town 0-1 Chertsey Town | Southern League - Premier South |
| 9 | Sat 20 Dec | 252-1 v BerkhamstedBerkhamsted 1-2 Chertsey Town | Southern League - Premier South |
| 10 | Sat 27 Dec | 250-1 v Walton & HershamChertsey Town 0-1 Walton & Hersham | Southern League - Premier South |
| 11 | Sat 10 Jan | 254-3 v Tiverton TownChertsey Town 4-3 Tiverton Town | Southern League - Premier South |
| 12 | Sat 24 Jan | 251-1 v Evesham UnitedEvesham United 1-1 Chertsey Town | Southern League - Premier South |
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