| 1 | Tue 3 Feb | 52-2 v Virginia WaterVirginia Water 2-2 Chessington & Hook United | Southern Combination Cup Second Round |
| 2 | Sat 14 Feb | 50-11 v CroydonCroydon 11-0 Chessington & Hook United | Southern Counties East League First Division |
| 3 | Tue 24 Feb | 54-1 v Welling TownChessington & Hook United 4-1 Welling Town | Southern Counties East League First Division |
| 4 | Sat 28 Feb | 51-2 v Halls AFCHalls AFC 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 5 | Sat 14 Mar | 63-2 v Banstead AthleticBanstead Athletic 2-3 Chessington & Hook United | Southern Counties East League First Division |
| 6 | Sat 21 Mar | 53-1 v Sheppey SportsChessington & Hook United 3-1 Sheppey Sports | Southern Counties East League First Division |
| 7 | Tue 24 Mar | 83-3 v FC ElmsteadChessington & Hook United 3-3 FC Elmstead | Southern Counties East League First Division |
| 8 | Sat 28 Mar | 70-7 v SE DonsSE Dons 7-0 Chessington & Hook United | Southern Counties East League First Division |
| 9 | Wed 1 Apr | 111-1 v GreenwaysChessington & Hook United 1-1 Greenways | Southern Counties East League First Division |
| 10 | Sat 4 Apr | 83-3 v Lydd TownChessington & Hook United 3-3 Lydd Town | Southern Counties East League First Division |
| 11 | Mon 6 Apr | 61-3 v CroydonChessington & Hook United 1-3 Croydon | Southern Counties East League First Division |
| 12 | Sat 11 Apr | 60-1 v SC ThamesmeadSC Thamesmead 1-0 Chessington & Hook United | Southern Counties East League First Division |
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