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Put 5 1/2 cups of the watermelon, 2 1/2 cups of the tomatoes, shallots, oil, vinegar, 2 tablespoons of the cilantro, salt and pepper into a blender and purée until smooth. Transfer purée to a fine mesh strainer set over a large bowl and strain, pressing as much through as possible; discard solids. Cover and chill for at least 1 hour.
Finely chop remaining 1/2 cup watermelon, 1/2 cup tomatoes and 2 tablespoons cilantro and toss together in a bowl. Pour chilled soup into bowls or glasses and top with watermelon-tomato mixture.