1. Preheat oven to 375°. In a roasting pan, toss tomatoes with garlic, sugar, dried oregano, a pinch each salt and pepper, and 1 tsp olive oil. Roast 25 minutes, until tomatoes begin to caramelize.
2. Meanwhile, cook fregola sarda as package directs.
3. Squeeze roasted garlic from skin; pulse in food processor with pine nuts, basil, a pinch each salt and pepper, and remaining 1 TBSP olive oil. Add Parmesan; pulse to combine.
4. In a bowl, combine fregola sarda, tomatoes, olives, goat cheese, and pesto. Scatter fresh oregano leaves on top, if desired.