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Dale Bryant scored twice for Sheerness East as they beat Kennington 3-2 in the Les Leckie Cup on Saturday.
Dale Wicketts got the other goal as they edged past their Ashford-based opponents.
Sheerness East will play Swale United in the next round on December 5 at the UK Paper Sports Ground.
AFC Sheppey suffered a 6-1 defeat at Premier in the Vandanel Kent County League, Division 1 East.
Scott Price scored Sheppey’s only goal against the Canterbury side.
Sheppey sit fifth in the table after seven league games. On Saturday they travel to Premier Division Bly Spartans in the Kent Intermediate Challenge Shield, second round.
Sheerness are in the same competition and face Tudor Sports at the Working Men’s Club in Halfway.