| 1 | Sat 26 Jul | 10-1 v BearstedHolmesdale 0-1 Bearsted | Southern Counties East League Premier Division |
| 2 | Sat 2 Aug | 11-1 v Tunbridge WellsTunbridge Wells 1-1 Holmesdale | Emirates FA Cup Extra Preliminary Round |
| 3 | Wed 6 Aug | 11-0 v Tunbridge WellsHolmesdale 1-0 Tunbridge Wells | Emirates FA Cup Extra Preliminary Round Replay |
| 4 | Sat 9 Aug | 11-4 v Faversham Strike ForceFaversham Strike Force 4-1 Holmesdale | Southern Counties East League Premier Division |
| 5 | Wed 13 Aug | 1 2-1 v Sutton AthleticHolmesdale 2-1 Sutton Athletic | Southern Counties East League Premier Division |
| 6 | Sat 16 Aug | 11-4 v Ashford UnitedAshford United 4-1 Holmesdale | Emirates FA Cup Preliminary Round |
| 7 | Sat 23 Aug | 10-4 v KenningtonKennington 4-0 Holmesdale | Southern Counties East League Premier Division |
| 8 | Mon 25 Aug | 14-1 v Chislehurst GlebeHolmesdale 4-1 Chislehurst Glebe | Southern Counties East League Premier Division |
| 9 | Sat 30 Aug | 16-2 v StansfeldHolmesdale 6-2 Stansfeld | Southern Counties East League Premier Division |
| 10 | Tue 2 Sep | 11-1 v Erith & BelvedereErith & Belvedere 1-1 Holmesdale | Southern Counties East League Premier Division |
| 11 | Sat 6 Sep | 12-0 v Tunbridge WellsTunbridge Wells 0-2 Holmesdale | Southern Counties East League Premier Division |
| 12 | Sat 13 Sep | 1 3-2 v CorinthianHolmesdale 3-2 Corinthian | Southern Counties East League Premier Division |
| 13 | Sat 20 Sep | 11-2 v Rochester UnitedHolmesdale 1-2 Rochester United | Isuzu FA Vase Second Qualifying Round |
| 14 | Tue 23 Sep | 10-4 v RusthallRusthall 4-0 Holmesdale | Southern Counties East League Premier Division |
| 15 | Sat 27 Sep | 13-1 v Hollands & BlairHollands & Blair 1-3 Holmesdale | Southern Counties East League Premier Division |
| 16 | Sat 4 Oct | 11-1 v Punjab UnitedHolmesdale 1-1 Punjab United | Southern Counties East League Premier Division |
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