| Wed 15/7/09 | Sittingbourne U18s 2-0 Sheerness East U18s |
Tues 11/8/09 | Crockenhill U18s 1-2 Sittingbourne U18s |
Sun 16/8/09 | Sittingbourne U18s 2-1 Bredhurst U18s |
Wed 19/8/09 | Sittingbourne U18s 3-1 Milton & Fulston U18s |
Sun 23/8/09 | Sittingbourne U18s 1-2 Dover Academy U18s |
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