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