Heat oven to 400 degrees. Toss butternut squash with 2 Tbsp. olive oil; season with salt and black pepper. Arrange coated squash on a baking sheet. Roast until squash is tender and lightly browned, 25 to 30 minutes, stirring once or twice.
In a blender, add the squash and broth; blend until smooth.
In a large pot, heat 1 tbsp. oil on medium-high heat. Add the garlic and shallots; cook for 2-3 minutes. Add the pureed butternut mixture, evaporated milk, cinnamon, cayenne pepper. Stir; salt and pepper to taste. Cook for an additional 5 minutes, or until heated through.