| 1 | Sat 6 Sep | 70-3 v Lordswood AFCLordswood AFC 3-0 Chessington & Hook United | Southern Counties East League First Division |
| 2 | Sat 13 Sep | 62-6 v SC ThamesmeadChessington & Hook United 2-6 SC Thamesmead | Southern Counties East League First Division |
| 3 | Sat 20 Sep | 70-2 v MoleseyMolesey 2-0 Chessington & Hook United | Isuzu FA Vase Second Qualifying Round |
| 4 | Tue 23 Sep | 60-2 v Tooting BecChessington & Hook United 0-2 Tooting Bec | Southern Counties East League First Division |
| 5 | Sat 27 Sep | 71-2 v Rochester UnitedRochester United 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 6 | Sat 4 Oct | 90-3 v SE DonsChessington & Hook United 0-3 SE Dons | Southern Counties East League First Division |
| 7 | Sat 11 Oct | 61-2 v Bridon RopesBridon Ropes 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 8 | Sat 25 Oct | 102-0 v Welling TownWelling Town 0-2 Chessington & Hook United | Southern Counties East League First Division |
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