In the oven, roast the halved and seeded butternut squash on a baking sheet at 400 degrees, until tender.
When tender, remove from oven and allow to cool enough to handle. Scoop the squash flesh out of the skins and set aside.
Melt butter in a large pot over medium heat. Add leeks and cook until soft. Being careful not to burn.
Add the squash flesh, garlic, apple, chicken broth, cider, and all of the spices. Increase temperature to high heat and bring the mixture to a low boil. Simmer until the apples soften. Turn off the heat and allow the mixture to cool for 5-10 minutes.
Using a stick blender, blend the soup in the pot until completely smooth. Be careful of hot liquid. If using a stand blender, puree soup in batches and cover the lid with a folded towel to protect yourself against splatters.
If the soup is too thick to blend, add a half cup of water to thin to the desired consistency.
Pour the blended soup back into the large pot and add the cream and sugar. Simmer over low heat until heated through.
Spoon into a small bowl and garnish with pepitas and chili oil with crunchy garlic, if desired. Serve with a hunk of crusty bread for a complete meal.