Ready!. Illustration shows Uncle Sam standing with a chip on his shoulder labeled Championship and clutching to his chest the America's Cup; a small yacht is at his feet, in the foreground, with a list of the years the United States has won the Cup. Sir Thomas Lipton is standing behind Uncle Sam, on a slip of land labeled England; he is trying to knock the chip of Uncle Sam's shoulder with a long staff labeled Challenge.. Date 1900 November 14. Ready!. Illustration shows Uncle Sam standing with a chip on his shoulder labeled Championship and clutching to his chest the America's Cup; a small yacht is at his feet, in the foreground, with a list of the years the United States has won the Cup. Sir Thomas Lipton is standing behind Uncle Sam, on a slip of land labeled England; he is trying to knock the chip of Uncle Sam's shoulder with a long staff labeled Challenge.. Date 1900 November 14.