| 1 | Sat 26 Jul | 100-1 v BearstedHolmesdale 0-1 Bearsted | Southern Counties East League Premier Division |
| 2 | Sat 2 Aug | 101-1 v Tunbridge WellsTunbridge Wells 1-1 Holmesdale | Emirates FA Cup Extra Preliminary Round |
| 3 | Wed 6 Aug | 101-0 v Tunbridge WellsHolmesdale 1-0 Tunbridge Wells | Emirates FA Cup Extra Preliminary Round Replay |
| 4 | Sat 9 Aug | 101-4 v Faversham Strike ForceFaversham Strike Force 4-1 Holmesdale | Southern Counties East League Premier Division |
| 5 | Wed 13 Aug | 102-1 v Sutton AthleticHolmesdale 2-1 Sutton Athletic | Southern Counties East League Premier Division |
| 6 | Sat 16 Aug | 101-4 v Ashford UnitedAshford United 4-1 Holmesdale | Emirates FA Cup Preliminary Round |
| 7 | Sat 23 Aug | 100-4 v KenningtonKennington 4-0 Holmesdale | Southern Counties East League Premier Division |
| 8 | Mon 25 Aug | 104-1 v Chislehurst GlebeHolmesdale 4-1 Chislehurst Glebe | Southern Counties East League Premier Division |
| 9 | Sat 30 Aug | 106-2 v StansfeldHolmesdale 6-2 Stansfeld | Southern Counties East League Premier Division |
| 10 | Tue 2 Sep | 101-1 v Erith & BelvedereErith & Belvedere 1-1 Holmesdale | Southern Counties East League Premier Division |
| 11 | Sat 6 Sep | 102-0 v Tunbridge WellsTunbridge Wells 0-2 Holmesdale | Southern Counties East League Premier Division |
| 12 | Sat 13 Sep | 103-2 v CorinthianHolmesdale 3-2 Corinthian | Southern Counties East League Premier Division |
| 13 | Tue 23 Sep | 100-4 v RusthallRusthall 4-0 Holmesdale | Southern Counties East League Premier Division |
| 14 | Sat 27 Sep | 103-1 v Hollands & BlairHollands & Blair 1-3 Holmesdale | Southern Counties East League Premier Division |
| 15 | Sat 4 Oct | 101-1 v Punjab UnitedHolmesdale 1-1 Punjab United | Southern Counties East League Premier Division |
| 16 | Wed 8 Oct | 101-0 v StansfeldStansfeld 0-1 Holmesdale | Southern Counties East League Premier Division |
| 17 | Sat 18 Oct | 10 0-5 v Larkfield & New HytheLarkfield & New Hythe 5-0 Holmesdale | Southern Counties East League Premier Division |
| 18 | Sat 25 Oct | 100-5 v Whitstable TownWhitstable Town 5-0 Holmesdale | Southern Counties East League Premier Division |
| 19 | Sat 1 Nov | 104-2 v Hythe TownHolmesdale 4-2 Hythe Town | Southern Counties East League Premier Division |
| 20 | Sat 8 Nov | 104-2 v Phoenix SportsHolmesdale 4-2 Phoenix Sports | Southern Counties East League Premier Division |
Football Web Pages