Preheat oven to 450°.
Combine first 3 ingredients on a large jelly-roll pan. Drizzle with 1 teaspoon oil; toss well. Coat squash mixture with cooking spray; arrange in a single layer. Bake at 450° for 15 minutes. Add tomatoes; turn vegetables with a spatula. Bake 5 minutes or until lightly browned. Remove from oven; cool on a wire rack 10 minutes.
Combine squash mixture, 1 teaspoon oil, olives, and remaining 5 ingredients in a bowl; toss gently. Serve immediately.