| 1 | Fri 24 Jul | 2 2-1 v Chislehurst GlebeChislehurst Glebe 1-2 Staplehurst Monarchs | Friendly |
| 2 | Sat 8 Aug | 23-1 v Bridon RopesBridon Ropes 1-3 Staplehurst Monarchs | Southern Counties East League First Division |
| 3 | Tue 18 Aug | 23-1 v Lordswood AFCStaplehurst Monarchs 3-1 Lordswood AFC | Southern Counties East League First Division |
| 4 | Sat 22 Aug | 2 1-0 v Lewisham BoroughStaplehurst Monarchs 1-0 Lewisham Borough | Southern Counties East League First Division |
| 5 | Mon 31 Aug | 20-4 v SC ThamesmeadStaplehurst Monarchs 0-4 SC Thamesmead | Southern Counties East League First Division |
| 6 | Sat 5 Sep | 20-0 v StansfeldStaplehurst Monarchs 0-0 Stansfeld | Southern Counties East League First Division |
| 7 | Sat 12 Sep | 2 1-2 v CorinthianCorinthian 2-1 Staplehurst Monarchs | FA Vase Second Qualifying Round |
| 8 | Wed 16 Sep | 23-2 v FC ElmsteadFC Elmstead 2-3 Staplehurst Monarchs | Southern Counties East League First Division |
| 9 | Sat 19 Sep | 22-0 v Lydd TownStaplehurst Monarchs 2-0 Lydd Town | Kent Senior Cup Preliminary Round |
| 10 | Sat 26 Sep | 20-0 v GreenwaysGreenways 0-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 11 | Sat 3 Oct | 22-2 v Hythe TownStaplehurst Monarchs 2-2 Hythe Town | Southern Counties East League First Division |
| 12 | Tue 13 Oct | 22-4 v Rochester UnitedStaplehurst Monarchs 2-4 Rochester United | Southern Counties East League First Division |
| 13 | Sat 17 Oct | 21-0 v BearstedStaplehurst Monarchs 1-0 Bearsted | Kent Senior Cup First Round |
| 14 | Sat 24 Oct | 22-1 v CroydonCroydon 1-2 Staplehurst Monarchs | Southern Counties East League First Division |
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