Preheat your oven to 400°F. Line a rimmed baking sheet with foil (for easy cleanup).
Bake bacon slices for 10 to 14 minutes, until they reach your preferred level of crispiness.
Transfer bacon to a plate and add cubed squash to the baking sheet. Stir the cubes so they get coated in the bacon drippings and sprinkle with salt and pepper.
Bake for 20 to 30 minutes, until squash is fork tender. Chop or crumble bacon and add it back to the hot pan. Bake for 1 additional minute to reheat and serve.