| 1 | Sat 10 Aug | 212-1 v Forest Hill ParkStaplehurst Monarchs 2-1 Forest Hill Park | Southern Counties East League First Division |
| 2 | Sat 17 Aug | 210-2 v CroydonStaplehurst Monarchs 0-2 Croydon | Southern Counties East League First Division |
| 3 | Sat 24 Aug | 215-3 v Forest RowForest Row 3-5 Staplehurst Monarchs | Isuzu FA Vase First Qualifying Round |
| 4 | Sat 7 Sep | 211-0 v Sheppey SportsStaplehurst Monarchs 1-0 Sheppey Sports | Southern Counties East League First Division |
| 5 | Wed 11 Sep | 212-2 v Canterbury CityStaplehurst Monarchs 2-2 Canterbury City | Southern Counties East League First Division |
| 6 | Sat 14 Sep | 213-0 v Welling TownWelling Town 0-3 Staplehurst Monarchs | Southern Counties East League First Division |
| 7 | Sat 21 Sep | 21 0-1 v PaghamStaplehurst Monarchs 0-1 Pagham | Isuzu FA Vase Second Qualifying Round |
| 8 | Tue 24 Sep | 212-0 v Rochester UnitedRochester United 0-2 Staplehurst Monarchs | Southern Counties East League First Division |
| 9 | Sat 28 Sep | 211-2 v Soul Tower HamletsStaplehurst Monarchs 1-2 Soul Tower Hamlets | Southern Counties East League First Division |
| 10 | Sat 5 Oct | 213-1 v GreenwaysGreenways 1-3 Staplehurst Monarchs | Southern Counties East League First Division |
| 11 | Sat 19 Oct | 210-1 v Bridon RopesBridon Ropes 1-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 12 | Wed 13 Nov | 211-0 v Whitstable TownStaplehurst Monarchs 1-0 Whitstable Town | P&Co SCEFL Challenge Cup Second Round |
| 13 | Sat 16 Nov | 211-2 v Clapton CommunityClapton Community 2-1 Staplehurst Monarchs | Southern Counties East League First Division |
| 14 | Sat 14 Dec | 210-1 v Halls AFCHalls AFC 1-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 15 | Sat 28 Dec | 213-0 v Canterbury CityCanterbury City 0-3 Staplehurst Monarchs | Southern Counties East League First Division |
| 16 | Sat 4 Jan | 210-5 v Sheppey SportsSheppey Sports 5-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 17 | Sat 25 Jan | 213-0 v Tooting BecStaplehurst Monarchs 3-0 Tooting Bec | Southern Counties East League First Division |
| 18 | Tue 28 Jan | 101-4 v Faversham TownFaversham Town 4-1 Staplehurst Monarchs | P&Co SCEFL Challenge Cup Third Round |
| 19 | Sat 1 Feb | 212-2 v SC ThamesmeadSC Thamesmead 2-2 Staplehurst Monarchs | Southern Counties East League First Division |
| 20 | Sat 22 Mar | 202-0 v GreenwaysStaplehurst Monarchs 2-0 Greenways | Southern Counties East League First Division |
| 21 | Wed 9 Apr | 20 0-2 v Faversham Strike ForceStaplehurst Monarchs 0-2 Faversham Strike Force | Southern Counties East League First Division |
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