| 1 | Sat 1 Nov | 112-5 v Halls AFCChessington & Hook United 2-5 Halls AFC | Southern Counties East League First Division |
| 2 | Sat 3 Jan | 34-8 v Sheppey SportsSheppey Sports 8-4 Chessington & Hook United | Southern Counties East League First Division |
| 3 | Sat 31 Jan | 92-2 v Tooting BecTooting Bec 2-2 Chessington & Hook United | Southern Counties East League First Division |
| 4 | Tue 3 Feb | 102-2 v Virginia WaterVirginia Water 2-2 Chessington & Hook United | Southern Combination Cup Second Round |
| 5 | Tue 24 Feb | 74-1 v Welling TownChessington & Hook United 4-1 Welling Town | Southern Counties East League First Division |
| 6 | Sat 28 Feb | 71-2 v Halls AFCHalls AFC 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 7 | Sat 14 Mar | 73-2 v Banstead AthleticBanstead Athletic 2-3 Chessington & Hook United | Southern Counties East League First Division |
| 8 | Tue 24 Mar | 73-3 v FC ElmsteadChessington & Hook United 3-3 FC Elmstead | Southern Counties East League First Division |
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