Preheat oven to 400˚F. Line a baking sheet with a silicone baking mat or parchment paper. Place butternut squash cut side up on the baking sheet.
In a small saucepan, bring the chicken stock to a simmer; cover and keep warm over low heat.
In a small bowl, stir together salt, cloves, nutmeg, and chili powder. Sprinkle over the squash evenly. Place 1 Tbsp butter in each well of the squash, reserving the final Tbsp butter for later.
Roast for 30 to 35 minutes, until fork tender (thicker squash may take longer). Scoop out squash into a large blender or food processor. Set aside.
While the squash is roasting, in a large high side skillet, heat 1 tbsp olive oil over medium heat. Add the garlic and cook until browned, about 1 minute. Stir in the rice and toast for 2 minutes. Add the wine and simmer until almost evaporated. Pour in approximately 1 cup of the hot stock. Cook, stirring constantly, until the stock has been absorbed. Repeat this process, adding 1 cup of stock at a time and stirring until the rice is tender. You may not need all the stock so test the rice between each addition. It should take approximately 25 to 35 minutes total.
Stir in parmesan cheese and butter until melted. Cover and set aside.
Add 2 Tbsp heavy cream to the squash and puree until smooth.
Stir in 1 1/2 cups puree (reserve rest for later! It's great for soup!), bacon, and sage. Season with salt and pepper to taste. Keep warm over low heat until ready to serve.