Preheat the oven to 450 degrees F (230 degrees C).
Combine butternut squash, cauliflower, and olive oil in a bowl and toss to combine. Spread out onto 1 or 2 baking sheets and season with salt, pepper, and curry powder. Add onion and garlic.
Toast in the preheated oven until vegetables are fork-tender and tips are crispy brown, about 20 minutes.
Add roasted vegetable mixture to a blender in batches with small amounts of chicken broth; blend until smooth. Transfer pureed vegetables to a large pot. Pour in remaining chicken broth. Season with additional salt, pepper, and curry powder to taste. Pour in half-and-half and sherry. Heat over medium heat until soup is hot, but do not allow to boil.
Ladle soup into bowls and top with goat cheese and crumbled bacon.