| 1 | Sat 27 Jul | 22-2 v Hollands & BlairHollands & Blair 2-2 Holmesdale | Southern Counties East League Premier Division |
| 2 | Sat 3 Aug | 30-1 v Crawley Down GatwickHolmesdale 0-1 Crawley Down Gatwick | Emirates FA Cup Extra Preliminary Round |
| 3 | Sat 10 Aug | 21-1 v Faversham TownHolmesdale 1-1 Faversham Town | Southern Counties East League Premier Division |
| 4 | Tue 13 Aug | 21-2 v Tunbridge WellsTunbridge Wells 2-1 Holmesdale | Southern Counties East League Premier Division |
| 5 | Sat 17 Aug | 24-3 v Lydd TownLydd Town 3-4 Holmesdale | Southern Counties East League Premier Division |
| 6 | Sat 24 Aug | 33-1 v StansfeldStansfeld 1-3 Holmesdale | Southern Counties East League Premier Division |
| 7 | Mon 26 Aug | 32-3 v GlebeHolmesdale 2-3 Glebe | Southern Counties East League Premier Division |
| 8 | Sat 31 Aug | 52-1 v Erith & BelvedereHolmesdale 2-1 Erith & Belvedere | Southern Counties East League Premier Division |
| 9 | Tue 3 Sep | 51-0 v FisherFisher 0-1 Holmesdale | Southern Counties East League Premier Division |
| 10 | Sat 7 Sep | 21-0 v CorinthianCorinthian 0-1 Holmesdale | Southern Counties East League Premier Division |
| 11 | Tue 10 Sep | 21-2 v Sutton AthleticHolmesdale 1-2 Sutton Athletic | Southern Counties East League Premier Division |
| 12 | Sat 14 Sep | 52-2 v Whitstable TownHolmesdale 2-2 Whitstable Town | Southern Counties East League Premier Division |
| 13 | Sat 28 Sep | 23-3 v Snodland TownHolmesdale 3-3 Snodland Town | Southern Counties East League Premier Division |
| 14 | Tue 1 Oct | 61-3 v Punjab UnitedHolmesdale 1-3 Punjab United | Southern Counties East League Premier Division |
| 15 | Sat 5 Oct | 6 2-2 v KenningtonHolmesdale 2-2 Kennington | Southern Counties East League Premier Division |
| 16 | Sat 19 Oct | 60-2 v RusthallRusthall 2-0 Holmesdale | Southern Counties East League Premier Division |
| 17 | Tue 22 Oct | 140-2 v FisherHolmesdale 0-2 Fisher | Southern Counties East League Premier Division |
| 18 | Sat 26 Oct | 121-1 v Larkfield & New HytheHolmesdale 1-1 Larkfield & New Hythe | Southern Counties East League Premier Division |
| 19 | Sat 2 Nov | 61-1 v KenningtonKennington 1-1 Holmesdale | Southern Counties East League Premier Division |
| 20 | Sat 9 Nov | 51-1 v Spelthorne SportsSpelthorne Sports 1-1 Holmesdale | Isuzu FA Vase Second Round |
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