| 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 | Sat 27 Sep | 21-2 v Rochester UnitedRochester United 2-1 Chessington & Hook United | Southern Counties East League First Division |
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