| 1 | Sat 20 Sep | 41-2 v Rochester UnitedHolmesdale 1-2 Rochester United | Isuzu FA Vase Second Qualifying Round |
| 2 | Tue 23 Sep | 140-4 v RusthallRusthall 4-0 Holmesdale | Southern Counties East League Premier Division |
| 3 | Sat 27 Sep | 143-1 v Hollands & BlairHollands & Blair 1-3 Holmesdale | Southern Counties East League Premier Division |
| 4 | Sat 4 Oct | 81-1 v Punjab UnitedHolmesdale 1-1 Punjab United | Southern Counties East League Premier Division |
| 5 | Wed 8 Oct | 161-0 v StansfeldStansfeld 0-1 Holmesdale | Southern Counties East League Premier Division |
| 6 | Sat 18 Oct | 160-5 v Larkfield & New HytheLarkfield & New Hythe 5-0 Holmesdale | Southern Counties East League Premier Division |
| 7 | Sat 6 Dec | 153-4 v Hollands & BlairHolmesdale 3-4 Hollands & Blair | Southern Counties East League Premier Division |
| 8 | Sat 13 Dec | 8 2-3 v Snodland TownSnodland Town 3-2 Holmesdale | Southern Counties East League Premier Division |
| 9 | Sat 20 Dec | 80-3 v Larkfield & New HytheHolmesdale 0-3 Larkfield & New Hythe | Southern Counties East League Premier Division |
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