| 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 |
| 6 | Tue 23 Sep | 50-2 v Tooting BecChessington & Hook United 0-2 Tooting Bec | Southern Counties East League First Division |
| 7 | Sat 4 Oct | 60-3 v SE DonsChessington & Hook United 0-3 SE Dons | Southern Counties East League First Division |
| 8 | Sat 11 Oct | 31-2 v Bridon RopesBridon Ropes 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 9 | Sat 25 Oct | 32-0 v Welling TownWelling Town 0-2 Chessington & Hook United | Southern Counties East League First Division |
| 10 | Sat 1 Nov | 62-5 v Halls AFCChessington & Hook United 2-5 Halls AFC | Southern Counties East League First Division |
| 11 | Sat 8 Nov | 30-1 v Lewisham BoroughLewisham Borough 1-0 Chessington & Hook United | Southern Counties East League First Division |
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