| 1 | Sat 2 Aug | 61-1 v Tunbridge WellsTunbridge Wells 1-1 Holmesdale | Emirates FA Cup Extra Preliminary Round |
| 2 | Wed 6 Aug | 61-0 v Tunbridge WellsHolmesdale 1-0 Tunbridge Wells | Emirates FA Cup Extra Preliminary Round Replay |
| 3 | Sat 9 Aug | 61-4 v Faversham Strike ForceFaversham Strike Force 4-1 Holmesdale | Southern Counties East League Premier Division |
| 4 | Wed 13 Aug | 62-1 v Sutton AthleticHolmesdale 2-1 Sutton Athletic | Southern Counties East League Premier Division |
| 5 | Sat 16 Aug | 61-4 v Ashford UnitedAshford United 4-1 Holmesdale | Emirates FA Cup Preliminary Round |
| 6 | Sat 23 Aug | 60-4 v KenningtonKennington 4-0 Holmesdale | Southern Counties East League Premier Division |
| 7 | Mon 25 Aug | 64-1 v Chislehurst GlebeHolmesdale 4-1 Chislehurst Glebe | Southern Counties East League Premier Division |
| 8 | Sat 30 Aug | 6 6-2 v StansfeldHolmesdale 6-2 Stansfeld | Southern Counties East League Premier Division |
| 9 | Tue 2 Sep | 61-1 v Erith & BelvedereErith & Belvedere 1-1 Holmesdale | Southern Counties East League Premier Division |
| 10 | Sat 13 Sep | 63-2 v CorinthianHolmesdale 3-2 Corinthian | Southern Counties East League Premier Division |
| 11 | Sat 20 Sep | 61-2 v Rochester UnitedHolmesdale 1-2 Rochester United | Isuzu FA Vase Second Qualifying Round |
| 12 | Tue 23 Sep | 60-4 v RusthallRusthall 4-0 Holmesdale | Southern Counties East League Premier Division |
| 13 | Sat 27 Sep | 63-1 v Hollands & BlairHollands & Blair 1-3 Holmesdale | Southern Counties East League Premier Division |
| 14 | Sat 4 Oct | 61-1 v Punjab UnitedHolmesdale 1-1 Punjab United | Southern Counties East League Premier Division |
| 15 | Wed 8 Oct | 6 1-0 v StansfeldStansfeld 0-1 Holmesdale | Southern Counties East League Premier Division |
| 16 | Sat 18 Oct | 60-5 v Larkfield & New HytheLarkfield & New Hythe 5-0 Holmesdale | Southern Counties East League Premier Division |
| 17 | Sat 25 Oct | 60-5 v Whitstable TownWhitstable Town 5-0 Holmesdale | Southern Counties East League Premier Division |
| 18 | Sat 1 Nov | 64-2 v Hythe TownHolmesdale 4-2 Hythe Town | Southern Counties East League Premier Division |
| 19 | Sat 8 Nov | 64-2 v Phoenix SportsHolmesdale 4-2 Phoenix Sports | Southern Counties East League Premier Division |
| 20 | Sat 22 Nov | 61-2 v Tunbridge WellsHolmesdale 1-2 Tunbridge Wells | Southern Counties East League Premier Division |
| 21 | Sat 29 Nov | 60-4 v BearstedBearsted 4-0 Holmesdale | Southern Counties East League Premier Division |
| 22 | Sat 6 Dec | 6 3-4 v Hollands & BlairHolmesdale 3-4 Hollands & Blair | Southern Counties East League Premier Division |
| 23 | Sat 13 Dec | 62-3 v Snodland TownSnodland Town 3-2 Holmesdale | Southern Counties East League Premier Division |
| 24 | Sat 20 Dec | 60-3 v Larkfield & New HytheHolmesdale 0-3 Larkfield & New Hythe | Southern Counties East League Premier Division |
| 25 | Sat 27 Dec | 62-1 v Chislehurst GlebeChislehurst Glebe 1-2 Holmesdale | Southern Counties East League Premier Division |
| 26 | Sat 10 Jan | 62-2 v Erith & BelvedereHolmesdale 2-2 Erith & Belvedere | Southern Counties East League Premier Division |
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