| 1 | Sat 2 Aug | 31-1 v AFC Greenwich BoroughAFC Greenwich Borough 1-1 Chessington & Hook United | Southern Counties East League First Division |
| 2 | Sat 23 Aug | 31-2 v Lydd TownLydd Town 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 3 | Sat 30 Aug | 30-1 v GreenwaysGreenways 1-0 Chessington & Hook United | Southern Counties East League First Division |
| 4 | Sat 6 Sep | 30-3 v Lordswood AFCLordswood AFC 3-0 Chessington & Hook United | Southern Counties East League First Division |
| 5 | Sat 20 Sep | 30-2 v MoleseyMolesey 2-0 Chessington & Hook United | Isuzu FA Vase Second Qualifying Round |
| 6 | Tue 23 Sep | 20-2 v Tooting BecChessington & Hook United 0-2 Tooting Bec | Southern Counties East League First Division |
| 7 | Sat 27 Sep | 31-2 v Rochester UnitedRochester United 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 8 | Sat 1 Nov | 32-5 v Halls AFCChessington & Hook United 2-5 Halls AFC | Southern Counties East League First Division |
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