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Preheat oven to 425 degrees. On a rimmed baking sheet, toss together squash, garlic, and 1 tablespoon oil and arrange in a single layer; season with salt and pepper. Bake until squash is soft and lightly golden, 20 to 25 minutes, tossing halfway through. Remove garlic from skins and toss with squash.
Meanwhile, in a large pot of boiling salted water, cook pasta 1 minute less than package instructions. Add kale and cook 1 minute. Reserve 1/2 cup pasta water, then drain. Return pasta and kale to pot, add squash mixture and remaining 2 tablespoons oil, and season with salt and pepper. Toss to combine, adding enough pasta water to create a light sauce that coats pasta. Serve topped with almonds.