| 1 | Sat 27 Jul | 32-2 v Hollands & BlairHollands & Blair 2-2 Holmesdale | Southern Counties East League Premier Division |
| 2 | Sat 3 Aug | 60-1 v Crawley Down GatwickHolmesdale 0-1 Crawley Down Gatwick | Emirates FA Cup Extra Preliminary Round |
| 3 | Sat 10 Aug | 31-1 v Faversham TownHolmesdale 1-1 Faversham Town | Southern Counties East League Premier Division |
| 4 | Tue 13 Aug | 31-2 v Tunbridge WellsTunbridge Wells 2-1 Holmesdale | Southern Counties East League Premier Division |
| 5 | Sat 17 Aug | 34-3 v Lydd TownLydd Town 3-4 Holmesdale | Southern Counties East League Premier Division |
| 6 | Sat 24 Aug | 43-1 v StansfeldStansfeld 1-3 Holmesdale | Southern Counties East League Premier Division |
| 7 | Mon 26 Aug | 52-3 v GlebeHolmesdale 2-3 Glebe | Southern Counties East League Premier Division |
| 8 | Sat 31 Aug | 162-1 v Erith & BelvedereHolmesdale 2-1 Erith & Belvedere | Southern Counties East League Premier Division |
| 9 | Tue 3 Sep | 31-0 v FisherFisher 0-1 Holmesdale | Southern Counties East League Premier Division |
| 10 | Sat 7 Sep | 31-0 v CorinthianCorinthian 0-1 Holmesdale | Southern Counties East League Premier Division |
| 11 | Tue 10 Sep | 31-2 v Sutton AthleticHolmesdale 1-2 Sutton Athletic | Southern Counties East League Premier Division |
| 12 | Sat 14 Sep | 32-2 v Whitstable TownHolmesdale 2-2 Whitstable Town | Southern Counties East League Premier Division |
| 13 | Tue 24 Sep | 61-1 v VCD AthleticVCD Athletic 1-1 Holmesdale | Southern Counties East League Premier Division |
| 14 | Sat 28 Sep | 63-3 v Snodland TownHolmesdale 3-3 Snodland Town | Southern Counties East League Premier Division |
| 15 | Tue 1 Oct | 31-3 v Punjab UnitedHolmesdale 1-3 Punjab United | Southern Counties East League Premier Division |
| 16 | Sat 5 Oct | 32-2 v KenningtonHolmesdale 2-2 Kennington | Southern Counties East League Premier Division |
| 17 | Tue 22 Oct | 30-2 v FisherHolmesdale 0-2 Fisher | Southern Counties East League Premier Division |
| 18 | Sat 26 Oct | 31-1 v Larkfield & New HytheHolmesdale 1-1 Larkfield & New Hythe | Southern Counties East League Premier Division |
| 19 | Sat 2 Nov | 41-1 v KenningtonKennington 1-1 Holmesdale | Southern Counties East League Premier Division |
| 20 | Sat 9 Nov | 41-1 v Spelthorne SportsSpelthorne Sports 1-1 Holmesdale | Isuzu FA Vase Second Round |
| 21 | Sat 16 Nov | 42-1 v Lordswood AFCLordswood AFC 1-2 Holmesdale | Southern Counties East League Premier Division |
| 22 | Sat 23 Nov | 42-1 v Halls AFCHalls AFC 1-2 Holmesdale | P&Co SCEFL Challenge Cup Second Round |
| 23 | Sat 30 Nov | 42-1 v BearstedHolmesdale 2-1 Bearsted | Southern Counties East League Premier Division |
| 24 | Sat 14 Dec | 42-3 v Punjab UnitedPunjab United 3-2 Holmesdale | Southern Counties East League Premier Division |
| 25 | Sat 21 Dec | 35-5 v VCD AthleticHolmesdale 5-5 VCD Athletic | Southern Counties East League Premier Division |
| 26 | Sat 28 Dec | 42-1 v StansfeldHolmesdale 2-1 Stansfeld | Southern Counties East League Premier Division |
| 27 | Sat 18 Jan | 40-0 v RusthallHolmesdale 0-0 Rusthall | P&Co SCEFL Challenge Cup Third Round |
| 28 | Sat 25 Jan | 44-1 v Lydd TownHolmesdale 4-1 Lydd Town | Southern Counties East League Premier Division |
| 29 | Sat 1 Feb | 42-5 v BearstedBearsted 5-2 Holmesdale | Southern Counties East League Premier Division |
| 30 | Wed 5 Feb | 41-2 v Forest Hill ParkForest Hill Park 2-1 Holmesdale | P&Co SCEFL Challenge Cup Quarter Final |
| 31 | Sat 15 Feb | 30-3 v Hollands & BlairHolmesdale 0-3 Hollands & Blair | Southern Counties East League Premier Division |
| 32 | Wed 19 Feb | 31-2 v GlebeGlebe 2-1 Holmesdale | Southern Counties East League Premier Division |
| 33 | Sat 1 Mar | 3 1-4 v RusthallHolmesdale 1-4 Rusthall | Southern Counties East League Premier Division |
| 34 | Sat 8 Mar | 42-1 v Lordswood AFCHolmesdale 2-1 Lordswood AFC | Southern Counties East League Premier Division |
| 35 | Sat 15 Mar | 34-3 v Larkfield & New HytheLarkfield & New Hythe 3-4 Holmesdale | Southern Counties East League Premier Division |
| 36 | Tue 18 Mar | 41-6 v Whitstable TownWhitstable Town 6-1 Holmesdale | Southern Counties East League Premier Division |
| 37 | Sat 22 Mar | 40-5 v Faversham TownFaversham Town 5-0 Holmesdale | Southern Counties East League Premier Division |
| 38 | Tue 25 Mar | 40-2 v Snodland TownSnodland Town 2-0 Holmesdale | Southern Counties East League Premier Division |
| 39 | Sat 5 Apr | 34-2 v CorinthianHolmesdale 4-2 Corinthian | Southern Counties East League Premier Division |
| 40 | Wed 16 Apr | 31-4 v Sutton AthleticSutton Athletic 4-1 Holmesdale | Southern Counties East League Premier Division |
| 41 | Mon 21 Apr | 63-1 v Erith & BelvedereErith & Belvedere 1-3 Holmesdale | Southern Counties East League Premier Division |
| 42 | Sat 26 Apr | 61-5 v Tunbridge WellsHolmesdale 1-5 Tunbridge Wells | Southern Counties East League Premier Division |
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