Preheat grill for medium heat and lightly oil the grate. Spray pineapple pieces with cooking spray.
Cook pineapple on the grill until lightly browned and caramelized, 5 to 10 minutes. Remove pineapple from grill and cool; chop.
Mix pineapple, red bell pepper, onion, cilantro, jalapeno pepper, garlic, lime juice, sugar, salt, and ground black pepper together in a bowl; refrigerate until chilled and flavors blend, about 1 hour.
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