Preheat oven to 400F. Line a baking sheet with parchment paper.
Cut the butternut squash into cubes, about 1-inch in size. Place on the baking sheet, drizzle with olive oil, garlic powder, salt and pepper and toss to combine.
Bake for 25 minutes. Remove from oven and set aside.
In a large pot, melt butter over medium heat. Add in flour and whisk until thickened. Slowly add in milk while whisking until combined.
Continue cooking over medium heat until mixture is thickened, stirring occasionally.
Add in cheese and stir until melted and creamy.
Add cooked butternut squash cubes to the pot and stir to combine. Cook for an additional 5 minutes or until heated through.