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Gillingham will travel to Hythe in the first round of the Kent Reliance Senior Cup.
The winners will then visit VCD Athletic in the second round.
Holders Dartford also enter at the first round stage, with a trip to Cray Wanderers, while Kent Reliance Senior Trophy winners Sheppey are rewarded with a tie at Ebbsfleet United.
Dates for the matches are to be confirmed.
There are three preliminary round matches in the Kent Reliance Senior Trophy, including Hollands & Blair at home to Snodland.
Last season's runners-up Ashford start their bid to win the trophy at Sutton Athletic in the first round.
Kent Reliance Senior Cup first round draw: Hythe v Gillingham, Chatham v Welling, Folkestone v Thamesmead, Ebbsfleet v Sheppey, Sittingbourne v Ramsgate, Bromley v Maidstone, Cray Wanderers v Dartford.
Second round: Phoenix Sports v Charlton, Tonbridge v Bromley or Maidstone, Greenwich v Margate, VCD v Hythe or Gillingham, Herne Bay v Dover, Sittingbourne or Ramsgate v Ebbsfleet or Sheppey, Faversham v Folkestone or Thamesmead, Chatham or Welling v Cray Wanderers or Dartford
Kent Reliance Senior Trophy Preliminary round draw: Gravesham Borough v Croydon, Holmesdale v K Sports, Hollands & Blair v Snodland Town (ties to be played on September 17).
First round: Rochester v Eltham Palace, Lordswood v SC Thamesmead, Beckenham v Sevenoaks, Fisher v Lydd, FC Elmstead v Kent Football Utd, AFC Croydon Ath v Erith Town, Corinthian v West Wickham, Meridian v Canterbury, Tunbridge Wells v Crockenhill, Rusthall v Erith & Belvedere, Deal v Holmesdale or K Sports, Cray Valley v Hollands & Blair or Snodland, Whitstable v Orpington, Glebe v Bearsted, Sutton Ath v Ashford, Lewisham Borough v Gravesham Borough or Croydon (ties to be played on October 15).