| 1 | Sat 26 Oct | 11-1 v Larkfield & New HytheHolmesdale 1-1 Larkfield & New Hythe | Southern Counties East League Premier Division |
| 2 | Sat 2 Nov | 11-1 v KenningtonKennington 1-1 Holmesdale | Southern Counties East League Premier Division |
| 3 | Sat 9 Nov | 11-1 v Spelthorne SportsSpelthorne Sports 1-1 Holmesdale | Isuzu FA Vase Second Round |
| 4 | Sat 16 Nov | 12-1 v Lordswood AFCLordswood AFC 1-2 Holmesdale | Southern Counties East League Premier Division |
| 5 | Sat 23 Nov | 12-1 v Halls AFCHalls AFC 1-2 Holmesdale | P&Co SCEFL Challenge Cup Second Round |
| 6 | Sat 30 Nov | 12-1 v BearstedHolmesdale 2-1 Bearsted | Southern Counties East League Premier Division |
| 7 | Sat 14 Dec | 12-3 v Punjab UnitedPunjab United 3-2 Holmesdale | Southern Counties East League Premier Division |
| 8 | Sat 21 Dec | 15-5 v VCD AthleticHolmesdale 5-5 VCD Athletic | Southern Counties East League Premier Division |
| 9 | Sat 28 Dec | 12-1 v StansfeldHolmesdale 2-1 Stansfeld | Southern Counties East League Premier Division |
| 10 | Sat 18 Jan | 10-0 v RusthallHolmesdale 0-0 Rusthall | P&Co SCEFL Challenge Cup Third Round |
| 11 | Sat 25 Jan | 14-1 v Lydd TownHolmesdale 4-1 Lydd Town | Southern Counties East League Premier Division |
| 12 | Sat 1 Feb | 12-5 v BearstedBearsted 5-2 Holmesdale | Southern Counties East League Premier Division |
| 13 | Wed 5 Feb | 11-2 v Forest Hill ParkForest Hill Park 2-1 Holmesdale | P&Co SCEFL Challenge Cup Quarter Final |
| 14 | Sat 15 Feb | 10-3 v Hollands & BlairHolmesdale 0-3 Hollands & Blair | Southern Counties East League Premier Division |
| 15 | Wed 19 Feb | 11-2 v GlebeGlebe 2-1 Holmesdale | Southern Counties East League Premier Division |
| 16 | Sat 1 Mar | 11-4 v RusthallHolmesdale 1-4 Rusthall | Southern Counties East League Premier Division |
| 17 | Sat 8 Mar | 12-1 v Lordswood AFCHolmesdale 2-1 Lordswood AFC | Southern Counties East League Premier Division |
| 18 | Sat 15 Mar | 14-3 v Larkfield & New HytheLarkfield & New Hythe 3-4 Holmesdale | Southern Counties East League Premier Division |
| 19 | Sat 22 Mar | 10-5 v Faversham TownFaversham Town 5-0 Holmesdale | Southern Counties East League Premier Division |
| 20 | Sat 5 Apr | 14-2 v CorinthianHolmesdale 4-2 Corinthian | Southern Counties East League Premier Division |
| 21 | Wed 16 Apr | 11-4 v Sutton AthleticSutton Athletic 4-1 Holmesdale | Southern Counties East League Premier Division |
| 22 | Mon 21 Apr | 13-1 v Erith & BelvedereErith & Belvedere 1-3 Holmesdale | Southern Counties East League Premier Division |
| 23 | Sat 26 Apr | 11-5 v Tunbridge WellsHolmesdale 1-5 Tunbridge Wells | Southern Counties East League Premier Division |
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