| 1 | Sat 10 Aug | 142-1 v Forest Hill ParkStaplehurst Monarchs 2-1 Forest Hill Park | Southern Counties East League First Division |
| 2 | Sat 17 Aug | 140-2 v CroydonStaplehurst Monarchs 0-2 Croydon | Southern Counties East League First Division |
| 3 | Sat 24 Aug | 145-3 v Forest RowForest Row 3-5 Staplehurst Monarchs | Isuzu FA Vase First Qualifying Round |
| 4 | Sat 31 Aug | 142-0 v Tooting BecTooting Bec 0-2 Staplehurst Monarchs | Southern Counties East League First Division |
| 5 | Sat 14 Sep | 143-0 v Welling TownWelling Town 0-3 Staplehurst Monarchs | Southern Counties East League First Division |
| 6 | Sat 21 Sep | 14 0-1 v PaghamStaplehurst Monarchs 0-1 Pagham | Isuzu FA Vase Second Qualifying Round |
| 7 | Tue 24 Sep | 142-0 v Rochester UnitedRochester United 0-2 Staplehurst Monarchs | Southern Counties East League First Division |
| 8 | Sat 28 Sep | 14 1-2 v Soul Tower HamletsStaplehurst Monarchs 1-2 Soul Tower Hamlets | Southern Counties East League First Division |
| 9 | Sat 26 Oct | 141-1 v SC ThamesmeadStaplehurst Monarchs 1-1 SC Thamesmead | Southern Counties East League First Division |
| 10 | Sat 2 Nov | 140-3 v Faversham Strike ForceFaversham Strike Force 3-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 11 | Sat 9 Nov | 141-2 v FC ElmsteadStaplehurst Monarchs 1-2 FC Elmstead | Southern Counties East League First Division |
| 12 | Wed 13 Nov | 141-0 v Whitstable TownStaplehurst Monarchs 1-0 Whitstable Town | P&Co SCEFL Challenge Cup Second Round |
| 13 | Sat 30 Nov | 15 1-1 v Soul Tower HamletsSoul Tower Hamlets 1-1 Staplehurst Monarchs | Southern Counties East League First Division |
| 14 | Sat 14 Dec | 140-1 v Halls AFCHalls AFC 1-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 15 | Sat 28 Dec | 143-0 v Canterbury CityCanterbury City 0-3 Staplehurst Monarchs | Southern Counties East League First Division |
| 16 | Sat 4 Jan | 140-5 v Sheppey SportsSheppey Sports 5-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 17 | Tue 28 Jan | 121-4 v Faversham TownFaversham Town 4-1 Staplehurst Monarchs | P&Co SCEFL Challenge Cup Third Round |
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