| 1 | Sat 26 Jul | 40-1 v BearstedHolmesdale 0-1 Bearsted | Southern Counties East League Premier Division |
| 2 | Wed 6 Aug | 4 1-0 v Tunbridge WellsHolmesdale 1-0 Tunbridge Wells | Emirates FA Cup Extra Preliminary Round Replay |
| 3 | Wed 13 Aug | 42-1 v Sutton AthleticHolmesdale 2-1 Sutton Athletic | Southern Counties East League Premier Division |
| 4 | Sat 30 Aug | 126-2 v StansfeldHolmesdale 6-2 Stansfeld | Southern Counties East League Premier Division |
| 5 | Tue 2 Sep | 121-1 v Erith & BelvedereErith & Belvedere 1-1 Holmesdale | Southern Counties East League Premier Division |
| 6 | Sat 20 Sep | 161-2 v Rochester UnitedHolmesdale 1-2 Rochester United | Isuzu FA Vase Second Qualifying Round |
| 7 | Sat 6 Dec | 43-4 v Hollands & BlairHolmesdale 3-4 Hollands & Blair | Southern Counties East League Premier Division |
| 8 | Sat 13 Dec | 42-3 v Snodland TownSnodland Town 3-2 Holmesdale | Southern Counties East League Premier Division |
| 9 | Sat 20 Dec | 40-3 v Larkfield & New HytheHolmesdale 0-3 Larkfield & New Hythe | Southern Counties East League Premier Division |
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