| 1 | Sat 16 Nov | 52-1 v Lordswood AFCLordswood AFC 1-2 Holmesdale | Southern Counties East League Premier Division |
| 2 | Sat 23 Nov | 52-1 v Halls AFCHalls AFC 1-2 Holmesdale | P&Co SCEFL Challenge Cup Second Round |
| 3 | Sat 30 Nov | 5 2-1 v BearstedHolmesdale 2-1 Bearsted | Southern Counties East League Premier Division |
| 4 | Sat 14 Dec | 5 2-3 v Punjab UnitedPunjab United 3-2 Holmesdale | Southern Counties East League Premier Division |
| 5 | Sat 21 Dec | 5 5-5 v VCD AthleticHolmesdale 5-5 VCD Athletic | Southern Counties East League Premier Division |
| 6 | Sat 28 Dec | 52-1 v StansfeldHolmesdale 2-1 Stansfeld | Southern Counties East League Premier Division |
| 7 | Sat 18 Jan | 50-0 v RusthallHolmesdale 0-0 Rusthall | P&Co SCEFL Challenge Cup Third Round |
| 8 | Sat 25 Jan | 54-1 v Lydd TownHolmesdale 4-1 Lydd Town | Southern Counties East League Premier Division |
| 9 | Sat 1 Feb | 52-5 v BearstedBearsted 5-2 Holmesdale | Southern Counties East League Premier Division |
| 10 | Wed 5 Feb | 51-2 v Forest Hill ParkForest Hill Park 2-1 Holmesdale | P&Co SCEFL Challenge Cup Quarter Final |
| 11 | Sat 15 Feb | 50-3 v Hollands & BlairHolmesdale 0-3 Hollands & Blair | Southern Counties East League Premier Division |
| 12 | Wed 19 Feb | 51-2 v GlebeGlebe 2-1 Holmesdale | Southern Counties East League Premier Division |
| 13 | Sat 1 Mar | 51-4 v RusthallHolmesdale 1-4 Rusthall | Southern Counties East League Premier Division |
| 14 | Sat 8 Mar | 52-1 v Lordswood AFCHolmesdale 2-1 Lordswood AFC | Southern Counties East League Premier Division |
| 15 | Sat 15 Mar | 54-3 v Larkfield & New HytheLarkfield & New Hythe 3-4 Holmesdale | Southern Counties East League Premier Division |
| 16 | Tue 18 Mar | 51-6 v Whitstable TownWhitstable Town 6-1 Holmesdale | Southern Counties East League Premier Division |
| 17 | Sat 22 Mar | 50-5 v Faversham TownFaversham Town 5-0 Holmesdale | Southern Counties East League Premier Division |
| 18 | Tue 25 Mar | 50-2 v Snodland TownSnodland Town 2-0 Holmesdale | Southern Counties East League Premier Division |
| 19 | Wed 16 Apr | 151-4 v Sutton AthleticSutton Athletic 4-1 Holmesdale | Southern Counties East League Premier Division |
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