| 1 | Sat 2 Aug | 21-1 v AFC Greenwich BoroughAFC Greenwich Borough 1-1 Chessington & Hook United | Southern Counties East League First Division |
| 2 | Sat 16 Aug | 30-0 v Staplehurst MonarchsChessington & Hook United 0-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 3 | Sat 23 Aug | 21-2 v Lydd TownLydd Town 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 4 | Mon 25 Aug | 21-3 v Banstead AthleticChessington & Hook United 1-3 Banstead Athletic | Southern Counties East League First Division |
| 5 | Sat 30 Aug | 2 0-1 v GreenwaysGreenways 1-0 Chessington & Hook United | Southern Counties East League First Division |
| 6 | Sat 6 Sep | 20-3 v Lordswood AFCLordswood AFC 3-0 Chessington & Hook United | Southern Counties East League First Division |
| 7 | Sat 13 Sep | 22-6 v SC ThamesmeadChessington & Hook United 2-6 SC Thamesmead | Southern Counties East League First Division |
| 8 | Sat 20 Sep | 20-2 v MoleseyMolesey 2-0 Chessington & Hook United | Isuzu FA Vase Second Qualifying Round |
| 9 | Tue 23 Sep | 80-2 v Tooting BecChessington & Hook United 0-2 Tooting Bec | Southern Counties East League First Division |
| 10 | Sat 27 Sep | 21-2 v Rochester UnitedRochester United 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 11 | Sat 4 Oct | 100-3 v SE DonsChessington & Hook United 0-3 SE Dons | Southern Counties East League First Division |
| 12 | Sat 11 Oct | 2 1-2 v Bridon RopesBridon Ropes 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 13 | Sat 13 Dec | 21-2 v Staplehurst MonarchsStaplehurst Monarchs 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 14 | Sat 3 Jan | 24-8 v Sheppey SportsSheppey Sports 8-4 Chessington & Hook United | Southern Counties East League First Division |
| 15 | Sat 31 Jan | 22-2 v Tooting BecTooting Bec 2-2 Chessington & Hook United | Southern Counties East League First Division |
| 16 | Tue 3 Feb | 22-2 v Virginia WaterVirginia Water 2-2 Chessington & Hook United | Southern Combination Cup Second Round |
| 17 | Sat 14 Feb | 20-11 v CroydonCroydon 11-0 Chessington & Hook United | Southern Counties East League First Division |
| 18 | Tue 24 Feb | 24-1 v Welling TownChessington & Hook United 4-1 Welling Town | Southern Counties East League First Division |
| 19 | Sat 28 Feb | 21-2 v Halls AFCHalls AFC 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 20 | Sat 14 Mar | 23-2 v Banstead AthleticBanstead Athletic 2-3 Chessington & Hook United | Southern Counties East League First Division |
| 21 | Sat 21 Mar | 23-1 v Sheppey SportsChessington & Hook United 3-1 Sheppey Sports | Southern Counties East League First Division |
| 22 | Tue 24 Mar | 33-3 v FC ElmsteadChessington & Hook United 3-3 FC Elmstead | Southern Counties East League First Division |
| 23 | Thu 26 Mar | 20-12 v CobhamCobham 12-0 Chessington & Hook United | Southern Combination Cup Quarter Final |
| 24 | Mon 30 Mar | 30-3 v Lordswood AFCChessington & Hook United 0-3 Lordswood AFC | Southern Counties East League First Division |
| 25 | Wed 1 Apr | 31-1 v GreenwaysChessington & Hook United 1-1 Greenways | Southern Counties East League First Division |
| 26 | Sat 4 Apr | 23-3 v Lydd TownChessington & Hook United 3-3 Lydd Town | Southern Counties East League First Division |
| 27 | Mon 6 Apr | 31-3 v CroydonChessington & Hook United 1-3 Croydon | Southern Counties East League First Division |
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