| 1 | Sat 26 Jul | 90-1 v BearstedHolmesdale 0-1 Bearsted | Southern Counties East League Premier Division |
| 2 | Sat 13 Sep | 12 3-2 v CorinthianHolmesdale 3-2 Corinthian | Southern Counties East League Premier Division |
| 3 | Sat 20 Sep | 101-2 v Rochester UnitedHolmesdale 1-2 Rochester United | Isuzu FA Vase Second Qualifying Round |
| 4 | Tue 23 Sep | 70-4 v RusthallRusthall 4-0 Holmesdale | Southern Counties East League Premier Division |
| 5 | Sat 27 Sep | 83-1 v Hollands & BlairHollands & Blair 1-3 Holmesdale | Southern Counties East League Premier Division |
| 6 | Sat 4 Oct | 111-1 v Punjab UnitedHolmesdale 1-1 Punjab United | Southern Counties East League Premier Division |
| 7 | Wed 8 Oct | 81-0 v StansfeldStansfeld 0-1 Holmesdale | Southern Counties East League Premier Division |
| 8 | Sat 18 Oct | 110-5 v Larkfield & New HytheLarkfield & New Hythe 5-0 Holmesdale | Southern Counties East League Premier Division |
| 9 | Sat 25 Oct | 150-5 v Whitstable TownWhitstable Town 5-0 Holmesdale | Southern Counties East League Premier Division |
| 10 | Sat 1 Nov | 84-2 v Hythe TownHolmesdale 4-2 Hythe Town | Southern Counties East League Premier Division |
| 11 | Sat 8 Nov | 84-2 v Phoenix SportsHolmesdale 4-2 Phoenix Sports | Southern Counties East League Premier Division |
| 12 | Sat 22 Nov | 81-2 v Tunbridge WellsHolmesdale 1-2 Tunbridge Wells | Southern Counties East League Premier Division |
| 13 | Sat 29 Nov | 8 0-4 v BearstedBearsted 4-0 Holmesdale | Southern Counties East League Premier Division |
| 14 | Sat 6 Dec | 83-4 v Hollands & BlairHolmesdale 3-4 Hollands & Blair | Southern Counties East League Premier Division |
| 15 | Sat 13 Dec | 182-3 v Snodland TownSnodland Town 3-2 Holmesdale | Southern Counties East League Premier Division |
| 16 | Sat 20 Dec | 150-3 v Larkfield & New HytheHolmesdale 0-3 Larkfield & New Hythe | Southern Counties East League Premier Division |
| 17 | Sat 27 Dec | 142-1 v Chislehurst GlebeChislehurst Glebe 1-2 Holmesdale | Southern Counties East League Premier Division |
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