| 1 | Sat 2 Aug | 101-1 v AFC Greenwich BoroughAFC Greenwich Borough 1-1 Chessington & Hook United | Southern Counties East League First Division |
| 2 | Sat 6 Sep | 140-3 v Lordswood AFCLordswood AFC 3-0 Chessington & Hook United | Southern Counties East League First Division |
| 3 | Sat 20 Sep | 90-2 v MoleseyMolesey 2-0 Chessington & Hook United | Isuzu FA Vase Second Qualifying Round |
| 4 | Tue 23 Sep | 30-2 v Tooting BecChessington & Hook United 0-2 Tooting Bec | Southern Counties East League First Division |
| 5 | Sat 27 Sep | 101-2 v Rochester UnitedRochester United 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 6 | Sat 4 Oct | 30-3 v SE DonsChessington & Hook United 0-3 SE Dons | Southern Counties East League First Division |
| 7 | Sat 11 Oct | 101-2 v Bridon RopesBridon Ropes 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 8 | Sat 1 Nov | 172-5 v Halls AFCChessington & Hook United 2-5 Halls AFC | Southern Counties East League First Division |
| 9 | Sat 8 Nov | 100-1 v Lewisham BoroughLewisham Borough 1-0 Chessington & Hook United | Southern Counties East League First Division |
| 10 | Sat 13 Dec | 141-2 v Staplehurst MonarchsStaplehurst Monarchs 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 11 | Sat 3 Jan | 124-8 v Sheppey SportsSheppey Sports 8-4 Chessington & Hook United | Southern Counties East League First Division |
| 12 | Sat 31 Jan | 122-2 v Tooting BecTooting Bec 2-2 Chessington & Hook United | Southern Counties East League First Division |
| 13 | Tue 3 Feb | 92-2 v Virginia WaterVirginia Water 2-2 Chessington & Hook United | Southern Combination Cup Second Round |
| 14 | Sat 14 Feb | 9 0-11 v CroydonCroydon 11-0 Chessington & Hook United | Southern Counties East League First Division |
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