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type
  TForm1 = class(TForm)
    PopupMenu1: TPopupMenu;
    Button1: TButton;
    procedure Button1Click(Sender: TObject);
  private
    { Private-Deklarationen }
    procedure Pop1Popup(Sender: TObject);
    procedure MyPopupHandler(Sender: TObject);
  public
    { Public-Deklarationen }
  end;

...

procedure TForm1.Pop1Popup(Sender: TObject);
var
  i: Integer;
  PopItem: TMenuItem;
begin
  with PopupMenu1 do for i := 0 to Items.Count - 1 do Items.Delete(0);

  for i := 0 to 10 do begin
    PopItem := TMenuItem.Create(Self);
    with PopItem do begin
      Caption := IntToStr(i);
      OnClick := MyPopupHandler;
      PopupMenu1.Items.Add(PopItem);
    end;
  end;
end;

procedure TForm1.MyPopupHandler(Sender: TObject);
begin
  with Sender as TMenuItem do begin
    ShowMessage( Caption );
  end;
end;

procedure TForm1.Button1Click(Sender: TObject);
begin
  Pop1Popup(Sender);
  Self.PopupMenu := PopupMenu1;
end;