| 1 | Fri 24 Jul | 112-1 v Chislehurst GlebeChislehurst Glebe 1-2 Staplehurst Monarchs | Friendly |
| 2 | Sat 8 Aug | 11 3-1 v Bridon RopesBridon Ropes 1-3 Staplehurst Monarchs | Southern Counties East League First Division |
| 3 | Tue 18 Aug | 113-1 v Lordswood AFCStaplehurst Monarchs 3-1 Lordswood AFC | Southern Counties East League First Division |
| 4 | Sat 22 Aug | 111-0 v Lewisham BoroughStaplehurst Monarchs 1-0 Lewisham Borough | Southern Counties East League First Division |
| 5 | Sat 12 Sep | 111-2 v CorinthianCorinthian 2-1 Staplehurst Monarchs | FA Vase Second Qualifying Round |
| 6 | Wed 16 Sep | 113-2 v FC ElmsteadFC Elmstead 2-3 Staplehurst Monarchs | Southern Counties East League First Division |
| 7 | Sat 26 Sep | 110-0 v GreenwaysGreenways 0-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 8 | Sat 3 Oct | 112-2 v Hythe TownStaplehurst Monarchs 2-2 Hythe Town | Southern Counties East League First Division |
| 9 | Tue 13 Oct | 11 2-4 v Rochester UnitedStaplehurst Monarchs 2-4 Rochester United | Southern Counties East League First Division |
| 10 | Sat 17 Oct | 111-0 v BearstedStaplehurst Monarchs 1-0 Bearsted | Kent Senior Cup First Round |
| 11 | Sat 24 Oct | 112-1 v CroydonCroydon 1-2 Staplehurst Monarchs | Southern Counties East League First Division |
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