| 1 | Wed 6 Aug | 21-0 v Tunbridge WellsHolmesdale 1-0 Tunbridge Wells | Emirates FA Cup Extra Preliminary Round Replay |
| 2 | Sat 9 Aug | 21-4 v Faversham Strike ForceFaversham Strike Force 4-1 Holmesdale | Southern Counties East League Premier Division |
| 3 | Wed 13 Aug | 2 2-1 v Sutton AthleticHolmesdale 2-1 Sutton Athletic | Southern Counties East League Premier Division |
| 4 | Sat 16 Aug | 21-4 v Ashford UnitedAshford United 4-1 Holmesdale | Emirates FA Cup Preliminary Round |
| 5 | Sat 23 Aug | 20-4 v KenningtonKennington 4-0 Holmesdale | Southern Counties East League Premier Division |
| 6 | Sat 20 Dec | 140-3 v Larkfield & New HytheHolmesdale 0-3 Larkfield & New Hythe | Southern Counties East League Premier Division |
| 7 | Sat 27 Dec | 122-1 v Chislehurst GlebeChislehurst Glebe 1-2 Holmesdale | Southern Counties East League Premier Division |
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