In 1959, Sir Roland Symonette, first Premier of the Bahama Islands, had donated a cup for the Star regattas in Nassau but, for a long time, it has never been awarded.
The Symonette family generously donated the Sir Roland Symonette Trophy to the Star Sailors League, thus it was won for the first time at the end of the 2013 Star Sailors League Finals. This perpetual trophy is awarded to the winning team of the Star Sailors League Finals.
In 2013, the Brazilian sailors Robert Scheidt and Bruno Prada were the first ever to have their names engraved on the silver cup. In 2015, George Szabo won the First SSL Lake Grand Slam and the SSL Finals with Edoardo Natucci. Last year Mark Mendelblatt and Brian Fatih were honored to engrave their names for the second time.