| 1 | Sat 9 Aug | 12-0 v Tiverton TownTiverton Town 0-2 Chertsey Town | Southern League - Premier South |
| 2 | Tue 12 Aug | 10-1 v BerkhamstedChertsey Town 0-1 Berkhamsted | Southern League - Premier South |
| 3 | Sat 16 Aug | 10-1 v Farnham TownChertsey Town 0-1 Farnham Town | Southern League - Premier South |
| 4 | Sat 23 Aug | 10-0 v Yate TownYate Town 0-0 Chertsey Town | Southern League - Premier South |
| 5 | Mon 25 Aug | 13-3 v UxbridgeChertsey Town 3-3 Uxbridge | Southern League - Premier South |
| 6 | Sat 6 Sep | 10-1 v Poole TownPoole Town 1-0 Chertsey Town | Southern League - Premier South |
| 7 | Sat 4 Oct | 11-2 v TilburyChertsey Town 1-2 Tilbury | Isuzu FA Trophy Third Qualifying Round |
| 8 | Tue 7 Oct | 13-3 v LeatherheadChertsey Town 3-3 Leatherhead | Surrey Senior Cup First Round |
| 9 | Sat 11 Oct | 12-0 v Taunton TownTaunton Town 0-2 Chertsey Town | Southern League - Premier South |
| 10 | Tue 14 Oct | 1 1-2 v Basingstoke TownBasingstoke Town 2-1 Chertsey Town | Southern League - Premier South |
| 11 | Sat 18 Oct | 11-1 v Bracknell TownChertsey Town 1-1 Bracknell Town | Southern League - Premier South |
| 12 | Tue 21 Oct | 11-1 v SholingChertsey Town 1-1 Sholing | Southern League - Premier South |
| 13 | Sat 1 Nov | 11-4 v Wimborne TownWimborne Town 4-1 Chertsey Town | Southern League - Premier South |
| 14 | Sat 8 Nov | 10-0 v Dorchester TownDorchester Town 0-0 Chertsey Town | Southern League - Premier South |
| 15 | Sat 15 Nov | 1 4-0 v Evesham UnitedChertsey Town 4-0 Evesham United | Southern League - Premier South |
| 16 | Tue 18 Nov | 12-1 v Hanwell TownChertsey Town 2-1 Hanwell Town | Southern League - Premier South |
| 17 | Sat 22 Nov | 10-2 v Gloucester CityGloucester City 2-0 Chertsey Town | Southern League - Premier South |
| 18 | Wed 26 Nov | 11-1 v Havant & WaterloovilleHavant & Waterlooville 1-1 Chertsey Town | Southern League - Premier South |
| 19 | Sat 29 Nov | 11-0 v Plymouth ParkwayChertsey Town 1-0 Plymouth Parkway | Southern League - Premier South |
| 20 | Sat 6 Dec | 14-0 v WeymouthChertsey Town 4-0 Weymouth | Southern League - Premier South |
| 21 | Sat 13 Dec | 11-0 v Hungerford TownHungerford Town 0-1 Chertsey Town | Southern League - Premier South |
| 22 | Sat 20 Dec | 12-1 v BerkhamstedBerkhamsted 1-2 Chertsey Town | Southern League - Premier South |
| 23 | Sat 27 Dec | 10-1 v Walton & HershamChertsey Town 0-1 Walton & Hersham | Southern League - Premier South |
| 24 | Sat 3 Jan | 11-0 v UxbridgeUxbridge 0-1 Chertsey Town | Southern League - Premier South |
| 25 | Sat 10 Jan | 14-3 v Tiverton TownChertsey Town 4-3 Tiverton Town | Southern League - Premier South |
| 26 | Sat 24 Jan | 11-1 v Evesham UnitedEvesham United 1-1 Chertsey Town | Southern League - Premier South |
| 27 | Sat 7 Feb | 12-2 v Gosport BoroughGosport Borough 2-2 Chertsey Town | Southern League - Premier South |
| 28 | Sat 14 Feb | 12-2 v Gloucester CityChertsey Town 2-2 Gloucester City | Southern League - Premier South |
| 29 | Sat 28 Feb | 14-2 v Bracknell TownBracknell Town 2-4 Chertsey Town | Southern League - Premier South |
| 30 | Tue 3 Mar | 12-1 v Dorchester TownChertsey Town 2-1 Dorchester Town | Southern League - Premier South |
| 31 | Sat 7 Mar | 14-2 v Basingstoke TownChertsey Town 4-2 Basingstoke Town | Southern League - Premier South |
| 32 | Tue 10 Mar | 13-1 v Taunton TownChertsey Town 3-1 Taunton Town | Southern League - Premier South |
| 33 | Sat 14 Mar | 10-4 v SholingSholing 4-0 Chertsey Town | Southern League - Premier South |
| 34 | Tue 17 Mar | 11-3 v Plymouth ParkwayPlymouth Parkway 3-1 Chertsey Town | Southern League - Premier South |
| 35 | Sat 21 Mar | 13-0 v Wimborne TownChertsey Town 3-0 Wimborne Town | Southern League - Premier South |
| 36 | Sat 28 Mar | 10-1 v Farnham TownFarnham Town 1-0 Chertsey Town | Southern League - Premier South |
| 37 | Fri 3 Apr | 12-2 v Yate TownChertsey Town 2-2 Yate Town | Southern League - Premier South |
| 38 | Mon 6 Apr | 12-1 v Walton & HershamWalton & Hersham 1-2 Chertsey Town | Southern League - Premier South |
| 39 | Sat 11 Apr | 10-1 v Poole TownChertsey Town 0-1 Poole Town | Southern League - Premier South |
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