Preheat your oven to 425 degrees. Spray a baking sheet with non-stick cooking spray. Place the honeynut squash halves on the baking sheet and drizzle tops with olive oil, salt, and pepper. Roast the honeynut squash for about 20 minutes or until tender. Remove the squash from the oven to cool.
Once the squash has cooled, scoop out the flesh, leaving a border around the edges and place the insides into a large mixing bowl.
Meanwhile, reduce the oven temperature to 350 degrees. In a large skillet preheated to medium-high heat add about 1 tbsp of olive oil to the skillet. Add the onion and cook for about 5 minutes or until softened. Stir in the garlic and continue to cook for another minute.
Next, add in the ground beef, breaking it up with a wooden spoon. Cook the meat until no longer pink about 5 to 7 minutes. Stir in the cumin, chili powder, salt, and pepper. Add in the corn, black beans, enchilada sauce, and reserved honeynut squash. Stir to combine.
Now, fill the honeynut squash boats with the beef mixture and top with cheese. Place the baking sheet back into the oven and let the cheese melt about 5 minutes.
Remove from oven and garnish with your favorite toppings!