| 1 | Sat 2 Aug | 111-1 v AFC Greenwich BoroughAFC Greenwich Borough 1-1 Chessington & Hook United | Southern Counties East League First Division |
| 2 | Sat 16 Aug | 110-0 v Staplehurst MonarchsChessington & Hook United 0-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 3 | Mon 25 Aug | 121-3 v Banstead AthleticChessington & Hook United 1-3 Banstead Athletic | Southern Counties East League First Division |
| 4 | Sat 30 Aug | 110-1 v GreenwaysGreenways 1-0 Chessington & Hook United | Southern Counties East League First Division |
| 5 | Sat 6 Sep | 110-3 v Lordswood AFCLordswood AFC 3-0 Chessington & Hook United | Southern Counties East League First Division |
| 6 | Sat 20 Sep | 60-2 v MoleseyMolesey 2-0 Chessington & Hook United | Isuzu FA Vase Second Qualifying Round |
| 7 | Tue 23 Sep | 90-2 v Tooting BecChessington & Hook United 0-2 Tooting Bec | Southern Counties East League First Division |
| 8 | Sat 27 Sep | 61-2 v Rochester UnitedRochester United 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 9 | Sat 4 Oct | 10-3 v SE DonsChessington & Hook United 0-3 SE Dons | Southern Counties East League First Division |
| 10 | Sat 11 Oct | 161-2 v Bridon RopesBridon Ropes 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 11 | Sat 13 Dec | 151-2 v Staplehurst MonarchsStaplehurst Monarchs 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 12 | Sat 31 Jan | 6 2-2 v Tooting BecTooting Bec 2-2 Chessington & Hook United | Southern Counties East League First Division |
| 13 | Tue 3 Feb | 152-2 v Virginia WaterVirginia Water 2-2 Chessington & Hook United | Southern Combination Cup Second Round |
| 14 | Sat 14 Feb | 110-11 v CroydonCroydon 11-0 Chessington & Hook United | Southern Counties East League First Division |
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