| 1 | Sat 16 Aug | 140-0 v Staplehurst MonarchsChessington & Hook United 0-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 2 | Sat 23 Aug | 141-2 v Lydd TownLydd Town 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 3 | Mon 25 Aug | 111-3 v Banstead AthleticChessington & Hook United 1-3 Banstead Athletic | Southern Counties East League First Division |
| 4 | Sat 30 Aug | 100-1 v GreenwaysGreenways 1-0 Chessington & Hook United | Southern Counties East League First Division |
| 5 | Sat 6 Sep | 100-3 v Lordswood AFCLordswood AFC 3-0 Chessington & Hook United | Southern Counties East League First Division |
| 6 | Sat 27 Sep | 121-2 v Rochester UnitedRochester United 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 7 | Sat 4 Oct | 50-3 v SE DonsChessington & Hook United 0-3 SE Dons | Southern Counties East League First Division |
| 8 | Sat 11 Oct | 121-2 v Bridon RopesBridon Ropes 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 9 | Sat 1 Nov | 122-5 v Halls AFCChessington & Hook United 2-5 Halls AFC | Southern Counties East League First Division |
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