| 1 | Sat 2 Aug | 17 1-1 v AFC Greenwich BoroughAFC Greenwich Borough 1-1 Chessington & Hook United | Southern Counties East League First Division |
| 2 | Sat 16 Aug | 17 0-0 v Staplehurst MonarchsChessington & Hook United 0-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 3 | Sat 20 Sep | 160-2 v MoleseyMolesey 2-0 Chessington & Hook United | Isuzu FA Vase Second Qualifying Round |
| 4 | Tue 23 Sep | 40-2 v Tooting BecChessington & Hook United 0-2 Tooting Bec | Southern Counties East League First Division |
| 5 | Sat 11 Oct | 81-2 v Bridon RopesBridon Ropes 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 6 | Sat 8 Nov | 60-1 v Lewisham BoroughLewisham Borough 1-0 Chessington & Hook United | Southern Counties East League First Division |
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