| 1 | Sat 11 Oct | 11-2 v Bridon RopesBridon Ropes 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 2 | Sat 25 Oct | 12-0 v Welling TownWelling Town 0-2 Chessington & Hook United | Southern Counties East League First Division |
| 3 | Sat 1 Nov | 12-5 v Halls AFCChessington & Hook United 2-5 Halls AFC | Southern Counties East League First Division |
| 4 | Sat 8 Nov | 10-1 v Lewisham BoroughLewisham Borough 1-0 Chessington & Hook United | Southern Counties East League First Division |
| 5 | Sat 13 Dec | 11-2 v Staplehurst MonarchsStaplehurst Monarchs 2-1 Chessington & Hook United | Southern Counties East League First Division |
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