| 1 | Sat 9 Aug | 91-4 v Faversham Strike ForceFaversham Strike Force 4-1 Holmesdale | Southern Counties East League Premier Division |
| 2 | Wed 13 Aug | 162-1 v Sutton AthleticHolmesdale 2-1 Sutton Athletic | Southern Counties East League Premier Division |
| 3 | Sat 16 Aug | 91-4 v Ashford UnitedAshford United 4-1 Holmesdale | Emirates FA Cup Preliminary Round |
| 4 | Sat 23 Aug | 90-4 v KenningtonKennington 4-0 Holmesdale | Southern Counties East League Premier Division |
| 5 | Mon 25 Aug | 94-1 v Chislehurst GlebeHolmesdale 4-1 Chislehurst Glebe | Southern Counties East League Premier Division |
| 6 | Sat 30 Aug | 96-2 v StansfeldHolmesdale 6-2 Stansfeld | Southern Counties East League Premier Division |
| 7 | Tue 2 Sep | 91-1 v Erith & BelvedereErith & Belvedere 1-1 Holmesdale | Southern Counties East League Premier Division |
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