| 1 | Sat 2 Aug | 141-1 v AFC Greenwich BoroughAFC Greenwich Borough 1-1 Chessington & Hook United | Southern Counties East League First Division |
| 2 | Mon 25 Aug | 171-3 v Banstead AthleticChessington & Hook United 1-3 Banstead Athletic | Southern Counties East League First Division |
| 3 | Sat 20 Sep | 100-2 v MoleseyMolesey 2-0 Chessington & Hook United | Isuzu FA Vase Second Qualifying Round |
| 4 | Tue 23 Sep | 140-2 v Tooting BecChessington & Hook United 0-2 Tooting Bec | Southern Counties East League First Division |
| 5 | Sat 27 Sep | 91-2 v Rochester UnitedRochester United 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 6 | Sat 3 Jan | 144-8 v Sheppey SportsSheppey Sports 8-4 Chessington & Hook United | Southern Counties East League First Division |
| 7 | Sat 31 Jan | 142-2 v Tooting BecTooting Bec 2-2 Chessington & Hook United | Southern Counties East League First Division |
| 8 | Tue 3 Feb | 142-2 v Virginia WaterVirginia Water 2-2 Chessington & Hook United | Southern Combination Cup Second Round |
| 9 | Tue 24 Feb | 104-1 v Welling TownChessington & Hook United 4-1 Welling Town | Southern Counties East League First Division |
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