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Preheat oven to 350°F. Combine shrimp, olive oil, salt and pepper in a large bowl, toss to coat. Transfer shrimp to a baking sheet and place in the oven. Bake for 12-15 minutes or until the shrimp are no longer opaque and cooked through. Remove from the oven and chill in the refrigerator.
Combine balsamic, sriracha, ketchup, horseradish, brown sugar and garlic in a medium bowl, whisk to combine the cocktail sauce. Refrigerate until ready to serve. To serve, peel shrimp (if necessary) and arrange on a platter with the cocktail on the side for dipping.
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