| 1 | Sat 13 Dec | 161-2 v Staplehurst MonarchsStaplehurst Monarchs 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 2 | Sat 3 Jan | 154-8 v Sheppey SportsSheppey Sports 8-4 Chessington & Hook United | Southern Counties East League First Division |
| 3 | Sat 31 Jan | 42-2 v Tooting BecTooting Bec 2-2 Chessington & Hook United | Southern Counties East League First Division |
| 4 | Tue 3 Feb | 42-2 v Virginia WaterVirginia Water 2-2 Chessington & Hook United | Southern Combination Cup Second Round |
| 5 | Sat 14 Feb | 40-11 v CroydonCroydon 11-0 Chessington & Hook United | Southern Counties East League First Division |
| 6 | Tue 24 Feb | 164-1 v Welling TownChessington & Hook United 4-1 Welling Town | Southern Counties East League First Division |
| 7 | Sat 14 Mar | 53-2 v Banstead AthleticBanstead Athletic 2-3 Chessington & Hook United | Southern Counties East League First Division |
| 8 | Sat 21 Mar | 83-1 v Sheppey SportsChessington & Hook United 3-1 Sheppey Sports | Southern Counties East League First Division |
| 9 | Tue 24 Mar | 173-3 v FC ElmsteadChessington & Hook United 3-3 FC Elmstead | Southern Counties East League First Division |
| 10 | Sat 28 Mar | 50-7 v SE DonsSE Dons 7-0 Chessington & Hook United | Southern Counties East League First Division |
| 11 | Wed 1 Apr | 121-1 v GreenwaysChessington & Hook United 1-1 Greenways | Southern Counties East League First Division |
| 12 | Sat 4 Apr | 53-3 v Lydd TownChessington & Hook United 3-3 Lydd Town | Southern Counties East League First Division |
| 13 | Mon 6 Apr | 151-3 v CroydonChessington & Hook United 1-3 Croydon | Southern Counties East League First Division |
| 14 | Wed 15 Apr | 60-4 v Rochester UnitedChessington & Hook United 0-4 Rochester United | Southern Counties East League First Division |
| 15 | Mon 20 Apr | 43-0 v Bridon RopesChessington & Hook United 3-0 Bridon Ropes | Southern Counties East League First Division |
| 16 | Wed 22 Apr | 41-6 v AFC Greenwich BoroughChessington & Hook United 1-6 AFC Greenwich Borough | Southern Counties East League First Division |
| 17 | Sat 25 Apr | 41-2 v FC ElmsteadFC Elmstead 2-1 Chessington & Hook United | Southern Counties East League First Division |
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