| 1 | Sat 2 Aug | 41-1 v AFC Greenwich BoroughAFC Greenwich Borough 1-1 Chessington & Hook United | Southern Counties East League First Division |
| 2 | Sat 16 Aug | 4 0-0 v Staplehurst MonarchsChessington & Hook United 0-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 3 | Sat 23 Aug | 111-2 v Lydd TownLydd Town 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 4 | Mon 25 Aug | 41-3 v Banstead AthleticChessington & Hook United 1-3 Banstead Athletic | Southern Counties East League First Division |
| 5 | Sat 30 Aug | 50-1 v GreenwaysGreenways 1-0 Chessington & Hook United | Southern Counties East League First Division |
| 6 | Sat 6 Sep | 40-3 v Lordswood AFCLordswood AFC 3-0 Chessington & Hook United | Southern Counties East League First Division |
| 7 | Tue 23 Sep | 150-2 v Tooting BecChessington & Hook United 0-2 Tooting Bec | Southern Counties East League First Division |
| 8 | Sat 27 Sep | 51-2 v Rochester UnitedRochester United 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 9 | Sat 4 Oct | 40-3 v SE DonsChessington & Hook United 0-3 SE Dons | Southern Counties East League First Division |
| 10 | Sat 11 Oct | 41-2 v Bridon RopesBridon Ropes 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 11 | Sat 25 Oct | 52-0 v Welling TownWelling Town 0-2 Chessington & Hook United | Southern Counties East League First Division |
| 12 | Sat 1 Nov | 52-5 v Halls AFCChessington & Hook United 2-5 Halls AFC | Southern Counties East League First Division |
| 13 | Sat 8 Nov | 50-1 v Lewisham BoroughLewisham Borough 1-0 Chessington & Hook United | Southern Counties East League First Division |
| 14 | Sat 13 Dec | 101-2 v Staplehurst MonarchsStaplehurst Monarchs 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 15 | Sat 3 Jan | 44-8 v Sheppey SportsSheppey Sports 8-4 Chessington & Hook United | Southern Counties East League First Division |
| 16 | Tue 24 Feb | 44-1 v Welling TownChessington & Hook United 4-1 Welling Town | Southern Counties East League First Division |
| 17 | Sat 28 Feb | 41-2 v Halls AFCHalls AFC 2-1 Chessington & Hook United | Southern Counties East League First Division |
| 18 | Sat 14 Mar | 43-2 v Banstead AthleticBanstead Athletic 2-3 Chessington & Hook United | Southern Counties East League First Division |
| 19 | Sat 21 Mar | 43-1 v Sheppey SportsChessington & Hook United 3-1 Sheppey Sports | Southern Counties East League First Division |
| 20 | Tue 24 Mar | 43-3 v FC ElmsteadChessington & Hook United 3-3 FC Elmstead | Southern Counties East League First Division |
| 21 | Sat 28 Mar | 40-7 v SE DonsSE Dons 7-0 Chessington & Hook United | Southern Counties East League First Division |
| 22 | Mon 30 Mar | 160-3 v Lordswood AFCChessington & Hook United 0-3 Lordswood AFC | Southern Counties East League First Division |
| 23 | Wed 1 Apr | 41-1 v GreenwaysChessington & Hook United 1-1 Greenways | Southern Counties East League First Division |
| 24 | Sat 4 Apr | 43-3 v Lydd TownChessington & Hook United 3-3 Lydd Town | Southern Counties East League First Division |
| 25 | Mon 6 Apr | 41-3 v CroydonChessington & Hook United 1-3 Croydon | Southern Counties East League First Division |
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