| 1 | Sat 4 Oct | 80-3 v SE DonsChessington & Hook United 0-3 SE Dons | Southern Counties East League First Division |
| 2 | Tue 3 Feb | 12-2 v Virginia WaterVirginia Water 2-2 Chessington & Hook United | Southern Combination Cup Second Round |
| 3 | Tue 24 Feb | 14-1 v Welling TownChessington & Hook United 4-1 Welling Town | Southern Counties East League First Division |
| 4 | Sat 28 Feb | 11-2 v Halls AFCHalls AFC 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 5 | Sat 14 Mar | 13-2 v Banstead AthleticBanstead Athletic 2-3 Chessington & Hook United | Southern Counties East League First Division |
| 6 | Sat 21 Mar | 13-1 v Sheppey SportsChessington & Hook United 3-1 Sheppey Sports | Southern Counties East League First Division |
| 7 | Tue 24 Mar | 13-3 v FC ElmsteadChessington & Hook United 3-3 FC Elmstead | Southern Counties East League First Division |
| 8 | Sat 28 Mar | 10-7 v SE DonsSE Dons 7-0 Chessington & Hook United | Southern Counties East League First Division |
| 9 | Mon 30 Mar | 10-3 v Lordswood AFCChessington & Hook United 0-3 Lordswood AFC | Southern Counties East League First Division |
| 10 | Sat 4 Apr | 13-3 v Lydd TownChessington & Hook United 3-3 Lydd Town | Southern Counties East League First Division |
| 11 | Mon 6 Apr | 11-3 v CroydonChessington & Hook United 1-3 Croydon | Southern Counties East League First Division |
| 12 | Wed 15 Apr | 10-4 v Rochester UnitedChessington & Hook United 0-4 Rochester United | Southern Counties East League First Division |
| 13 | Sat 18 Apr | 12-3 v Lewisham BoroughChessington & Hook United 2-3 Lewisham Borough | Southern Counties East League First Division |
| 14 | Sat 25 Apr | 11-2 v FC ElmsteadFC Elmstead 2-1 Chessington & Hook United | Southern Counties East League First Division |
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