"John Ullmann" Kent Senior Cup 2008-09
First Round
- Ebbsfleet United 1-0 Dover Athletic
- Chatham Town 0-6 Folkestone Invicta
- Cray Wanderers 1-2 Ramsgate
- Whitstable Town 2-2 Tonbridge Angels (Whitstable won 5-4 on penalties)
- Thamesmead Town 3-1 Ashford Town
- Welling United 3-2 Sittingbourne
- Maidstone United 2-1 Margate
- Bromley 4-2 Dartford
Quarter Finals
- Maidstone United 0-2 Bromley
- Welling United 7-1 Folkestone Invicta
- Ramsgate 3-2 Thamesmead Town
- Whitstable Town 2-1 Ebbsfleet United
Semi-Finals
- Welling United 3-1 Ramsgate
- Bromley 2-3 Whitstable Town
Final (@ Welling United, 16/4/09)
- Welling United 6-1 Whitstablle Town
Kent Senior Trophy 2008-09
Sponsored by Umbro
First Round
- V C D Athletic 1-0 Bearsted
- Holmesdale 2-1 Hythe Town
- Lordswood 2-1 Milton & Fulston United
- West Wickham 4-0 Norton Sports
- Greenwich Borough 1-2 Sevenoaks Town
Second Round
- Faversham Town 2-3 Orpington
- Erith & Belvedere 3-1 Lordswood
- Beckenham Town 0-1 West Wickham
- Slade Green 1-7 Tunbridge Wells
- Erith Town 1-3 Herne Bay
- V C D Athletic 4-0 Crockenhill
- Deal Town 2-1 Holmesdale
- Sevenoaks Town 3-2 Croydon
Quarter Finals
- Orpington 0-2 Erith & Belvedere
- Deal Town 2-0 Tunbridge Wells
- Sevenoaks Town 1-2 West Wickham
- Herne Bay 2-7 V C D Athletic
Semi-Finals
- Deal Town 1-1 Erith & Belvedere (Erith won 6-5 on penalties)
- V C D Athletic 2-0 West Wickham
Final (@ Welling United, 19/4/09)
- Erith & Belvedere 2-3 V C D Athletic
2008-09 Cups Summary
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