| 1 | Sat 31 Aug | 162-0 v Tooting BecTooting Bec 0-2 Staplehurst Monarchs | Southern Counties East League First Division |
| 2 | Sat 7 Sep | 161-0 v Sheppey SportsStaplehurst Monarchs 1-0 Sheppey Sports | Southern Counties East League First Division |
| 3 | Wed 11 Sep | 162-2 v Canterbury CityStaplehurst Monarchs 2-2 Canterbury City | Southern Counties East League First Division |
| 4 | Sat 21 Sep | 160-1 v PaghamStaplehurst Monarchs 0-1 Pagham | Isuzu FA Vase Second Qualifying Round |
| 5 | Tue 24 Sep | 162-0 v Rochester UnitedRochester United 0-2 Staplehurst Monarchs | Southern Counties East League First Division |
| 6 | Sat 28 Sep | 161-2 v Soul Tower HamletsStaplehurst Monarchs 1-2 Soul Tower Hamlets | Southern Counties East League First Division |
| 7 | Sat 5 Oct | 16 3-1 v GreenwaysGreenways 1-3 Staplehurst Monarchs | Southern Counties East League First Division |
| 8 | Sat 26 Oct | 161-1 v SC ThamesmeadStaplehurst Monarchs 1-1 SC Thamesmead | Southern Counties East League First Division |
| 9 | Sat 2 Nov | 160-3 v Faversham Strike ForceFaversham Strike Force 3-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 10 | Sat 9 Nov | 161-2 v FC ElmsteadStaplehurst Monarchs 1-2 FC Elmstead | Southern Counties East League First Division |
| 11 | Wed 13 Nov | 161-0 v Whitstable TownStaplehurst Monarchs 1-0 Whitstable Town | P&Co SCEFL Challenge Cup Second Round |
| 12 | Sat 30 Nov | 7 1-1 v Soul Tower HamletsSoul Tower Hamlets 1-1 Staplehurst Monarchs | Southern Counties East League First Division |
| 13 | Sat 25 Jan | 163-0 v Tooting BecStaplehurst Monarchs 3-0 Tooting Bec | Southern Counties East League First Division |
| 14 | Sat 1 Feb | 162-2 v SC ThamesmeadSC Thamesmead 2-2 Staplehurst Monarchs | Southern Counties East League First Division |
| 15 | Wed 19 Feb | 163-1 v Rochester UnitedStaplehurst Monarchs 3-1 Rochester United | Southern Counties East League First Division |
| 16 | Sat 8 Mar | 160-2 v Bridon RopesStaplehurst Monarchs 0-2 Bridon Ropes | Southern Counties East League First Division |
| 17 | Wed 12 Mar | 161-2 v Welling TownStaplehurst Monarchs 1-2 Welling Town | Southern Counties East League First Division |
| 18 | Sat 22 Mar | 162-0 v GreenwaysStaplehurst Monarchs 2-0 Greenways | Southern Counties East League First Division |
| 19 | Sat 26 Apr | 162-1 v Halls AFCStaplehurst Monarchs 2-1 Halls AFC | Southern Counties East League First Division |
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