In 1950, Simpkins took both the league title and the National Challenge Cup. While most National Cups have been decided in a single game, this year the organizers opted for a home and away series. On April 22, 1950, Simpkins defeated Fall River Ponta Delgada 2-0. The second leg, held on May 7, 1950, ended in a 1-1 tie with Simpkins taking the title on aggregate. It was this year that Simpkins contributed five of its players to the U.S. team at the 1950 FIFA World Cup. In that tournament, the U.S. went 1-2, but its victory was the greatest upset of World Cup history as the U.S. defeated heavy favorites England.
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