| 1 | Sat 20 Sep | 140-2 v MoleseyMolesey 2-0 Chessington & Hook United | Isuzu FA Vase Second Qualifying Round |
| 2 | Tue 23 Sep | 120-2 v Tooting BecChessington & Hook United 0-2 Tooting Bec | Southern Counties East League First Division |
| 3 | Sat 27 Sep | 141-2 v Rochester UnitedRochester United 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 4 | Sat 1 Nov | 142-5 v Halls AFCChessington & Hook United 2-5 Halls AFC | Southern Counties East League First Division |
| 5 | Sat 21 Mar | 153-1 v Sheppey SportsChessington & Hook United 3-1 Sheppey Sports | Southern Counties East League First Division |
| 6 | Thu 26 Mar | 110-12 v CobhamCobham 12-0 Chessington & Hook United | Southern Combination Cup Quarter Final |
| 7 | Mon 30 Mar | 140-3 v Lordswood AFCChessington & Hook United 0-3 Lordswood AFC | Southern Counties East League First Division |
| 8 | Sat 4 Apr | 143-3 v Lydd TownChessington & Hook United 3-3 Lydd Town | Southern Counties East League First Division |
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