| 1 | Sat 20 Sep | 11 0-2 v MoleseyMolesey 2-0 Chessington & Hook United | Isuzu FA Vase Second Qualifying Round |
| 2 | Tue 23 Sep | 110-2 v Tooting BecChessington & Hook United 0-2 Tooting Bec | Southern Counties East League First Division |
| 3 | Sat 11 Oct | 111-2 v Bridon RopesBridon Ropes 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 4 | Sat 25 Oct | 42-0 v Welling TownWelling Town 0-2 Chessington & Hook United | Southern Counties East League First Division |
| 5 | Sat 1 Nov | 4 2-5 v Halls AFCChessington & Hook United 2-5 Halls AFC | Southern Counties East League First Division |
| 6 | Sat 8 Nov | 40-1 v Lewisham BoroughLewisham Borough 1-0 Chessington & Hook United | Southern Counties East League First Division |
| 7 | Sat 13 Dec | 41-2 v Staplehurst MonarchsStaplehurst Monarchs 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 8 | Mon 6 Apr | 131-3 v CroydonChessington & Hook United 1-3 Croydon | Southern Counties East League First Division |
| 9 | Sat 11 Apr | 110-1 v SC ThamesmeadSC Thamesmead 1-0 Chessington & Hook United | Southern Counties East League First Division |
| 10 | Wed 15 Apr | 80-4 v Rochester UnitedChessington & Hook United 0-4 Rochester United | Southern Counties East League First Division |
| 11 | Sat 18 Apr | 102-3 v Lewisham BoroughChessington & Hook United 2-3 Lewisham Borough | Southern Counties East League First Division |
| 12 | Mon 20 Apr | 113-0 v Bridon RopesChessington & Hook United 3-0 Bridon Ropes | Southern Counties East League First Division |
| 13 | Wed 22 Apr | 111-6 v AFC Greenwich BoroughChessington & Hook United 1-6 AFC Greenwich Borough | Southern Counties East League First Division |
| 14 | Sat 25 Apr | 111-2 v FC ElmsteadFC Elmstead 2-1 Chessington & Hook United | Southern Counties East League First Division |
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