Arrange a rack in the middle of the oven and heat the oven to 425°F.
Trim ends off 2 medium delicata squash. Cut in half lengthwise and use a spoon to scrape out the seeds and pulp. Cut into 1/2-inch-thick half-moons.
Place the squash on a rimmed baking sheet. Drizzle with 2 tablespoons olive oil, sprinkle with 1 teaspoon kosher salt and 1/4 teaspoon black pepper and toss to coat. Arrange the squash in a single layer.
Roast until lightly browned on the bottom, about 10 minutes. Use a thin spatula to flip the squash. Roast until the squash is tender and caramelized, 10 to 15 minutes more.