Preheat the oven to 400°F. Cut the butternut squash in half lengthwise. Remove the seeds and webbing of the squash.
Drizzle the squash halves with olive oil and season with salt and pepper. Place the squash cut side down on a baking sheet.
Roast for 30-40 minutes. The squash will start to brown on the outside. When done, it should be fork tender yet still slightly firm. Remove from the oven and let cool until it can be easily handled.