| 1 | Sat 16 Aug | 120-0 v Staplehurst MonarchsChessington & Hook United 0-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 2 | Sat 23 Aug | 4 1-2 v Lydd TownLydd Town 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 3 | Sat 6 Sep | 60-3 v Lordswood AFCLordswood AFC 3-0 Chessington & Hook United | Southern Counties East League First Division |
| 4 | Sat 13 Sep | 32-6 v SC ThamesmeadChessington & Hook United 2-6 SC Thamesmead | Southern Counties East League First Division |
| 5 | Sat 20 Sep | 50-2 v MoleseyMolesey 2-0 Chessington & Hook United | Isuzu FA Vase Second Qualifying Round |
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