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Preheat an outdoor grill or cast-iron grill pan. Once hot, place the watermelon disc down on the grill to caramelize and mark, about 2-3 minutes. With tongs or a large spatula, flip the watermelon and grill another 2-3 minutes. Remove watermelon to a cutting board and let rest for about 5 minutes.
Season grilled watermelon with salt and pepper. Top with prosciutto, Parmigiano and arugula, and garnish with balsamic drizzle. Slice into 6-8 "pizza" slices and serve.