Preheat oven to 375°F (190°C). Place garlic and squash (cut-side down) on parchment paper-lined baking sheet. Brush with 1 tsp (5 mL) of olive oil and season with salt and pepper. Roast until tender, about 40 min. Squeeze out garlic and scoop out squash, discarding skins. With a fork, mash garlic and squash together.
Step 2
Heat 2 tsp (10 mL) olive oil in a heavy-bottomed, medium-size saucepan over medium heat. Add onion and sauté, stirring until translucent, about 3 min. Add the rice, stirring to coat in oil until lightly toasted, about 2 min. Then, add squash mixture.
Step 3
Add wine and stir until almost fully absorbed. Then, add chicken broth one cup (250 mL) at a time. Stir often, letting rice almost fully absorb broth before adding another cup.
Step 4
Continue cooking until rice is creamy, cooked through but still firm to the bite, about 20 min. Stir in Parmesan cheese and pepper. Serve with a drizzle of the remaining olive oil and a shaving of fresh Parmesan if desired.
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