| 1 | Sat 10 Aug | 122-1 v Forest Hill ParkStaplehurst Monarchs 2-1 Forest Hill Park | Southern Counties East League First Division |
| 2 | Sat 17 Aug | 20-2 v CroydonStaplehurst Monarchs 0-2 Croydon | Southern Counties East League First Division |
| 3 | Sat 24 Aug | 25-3 v Forest RowForest Row 3-5 Staplehurst Monarchs | Isuzu FA Vase First Qualifying Round |
| 4 | Sat 31 Aug | 22-0 v Tooting BecTooting Bec 0-2 Staplehurst Monarchs | Southern Counties East League First Division |
| 5 | Sat 7 Sep | 21-0 v Sheppey SportsStaplehurst Monarchs 1-0 Sheppey Sports | Southern Counties East League First Division |
| 6 | Wed 11 Sep | 22-2 v Canterbury CityStaplehurst Monarchs 2-2 Canterbury City | Southern Counties East League First Division |
| 7 | Sat 14 Sep | 43-0 v Welling TownWelling Town 0-3 Staplehurst Monarchs | Southern Counties East League First Division |
| 8 | Sat 21 Sep | 20-1 v PaghamStaplehurst Monarchs 0-1 Pagham | Isuzu FA Vase Second Qualifying Round |
| 9 | Tue 24 Sep | 22-0 v Rochester UnitedRochester United 0-2 Staplehurst Monarchs | Southern Counties East League First Division |
| 10 | Sat 5 Oct | 2 3-1 v GreenwaysGreenways 1-3 Staplehurst Monarchs | Southern Counties East League First Division |
| 11 | Sat 19 Oct | 20-1 v Bridon RopesBridon Ropes 1-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 12 | Sat 26 Oct | 21-1 v SC ThamesmeadStaplehurst Monarchs 1-1 SC Thamesmead | Southern Counties East League First Division |
| 13 | Sat 2 Nov | 20-3 v Faversham Strike ForceFaversham Strike Force 3-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 14 | Sat 9 Nov | 21-2 v FC ElmsteadStaplehurst Monarchs 1-2 FC Elmstead | Southern Counties East League First Division |
| 15 | Wed 13 Nov | 21-0 v Whitstable TownStaplehurst Monarchs 1-0 Whitstable Town | P&Co SCEFL Challenge Cup Second Round |
| 16 | Sat 16 Nov | 21-2 v Clapton CommunityClapton Community 2-1 Staplehurst Monarchs | Southern Counties East League First Division |
| 17 | Sat 30 Nov | 21-1 v Soul Tower HamletsSoul Tower Hamlets 1-1 Staplehurst Monarchs | Southern Counties East League First Division |
| 18 | Sat 14 Dec | 20-1 v Halls AFCHalls AFC 1-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 19 | Sat 28 Dec | 23-0 v Canterbury CityCanterbury City 0-3 Staplehurst Monarchs | Southern Counties East League First Division |
| 20 | Sat 25 Jan | 23-0 v Tooting BecStaplehurst Monarchs 3-0 Tooting Bec | Southern Counties East League First Division |
| 21 | Tue 28 Jan | 21-4 v Faversham TownFaversham Town 4-1 Staplehurst Monarchs | P&Co SCEFL Challenge Cup Third Round |
| 22 | Sat 1 Feb | 22-2 v SC ThamesmeadSC Thamesmead 2-2 Staplehurst Monarchs | Southern Counties East League First Division |
| 23 | Wed 19 Feb | 2 3-1 v Rochester UnitedStaplehurst Monarchs 3-1 Rochester United | Southern Counties East League First Division |
| 24 | Sat 22 Feb | 20-1 v CroydonCroydon 1-0 Staplehurst Monarchs | Southern Counties East League First Division |
| 25 | Sat 8 Mar | 20-2 v Bridon RopesStaplehurst Monarchs 0-2 Bridon Ropes | Southern Counties East League First Division |
| 26 | Wed 12 Mar | 21-2 v Welling TownStaplehurst Monarchs 1-2 Welling Town | Southern Counties East League First Division |
| 27 | Sat 15 Mar | 22-2 v Forest Hill ParkForest Hill Park 2-2 Staplehurst Monarchs | Southern Counties East League First Division |
| 28 | Wed 19 Mar | 21-2 v Lewisham BoroughStaplehurst Monarchs 1-2 Lewisham Borough | Southern Counties East League First Division |
| 29 | Sat 22 Mar | 22-0 v GreenwaysStaplehurst Monarchs 2-0 Greenways | Southern Counties East League First Division |
| 30 | Sat 29 Mar | 22-1 v Lewisham BoroughLewisham Borough 1-2 Staplehurst Monarchs | Southern Counties East League First Division |
| 31 | Sat 5 Apr | 21-0 v Clapton CommunityStaplehurst Monarchs 1-0 Clapton Community | Southern Counties East League First Division |
| 32 | Wed 9 Apr | 20-2 v Faversham Strike ForceStaplehurst Monarchs 0-2 Faversham Strike Force | Southern Counties East League First Division |
| 33 | Sat 19 Apr | 22-0 v Meridian VPStaplehurst Monarchs 2-0 Meridian VP | Southern Counties East League First Division |
| 34 | Sat 26 Apr | 22-1 v Halls AFCStaplehurst Monarchs 2-1 Halls AFC | Southern Counties East League First Division |
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