Preheat oven to 350 degrees.
Cut spahetti squash length width wise, then length wise. Drizzle oil onto a cookie sheet. Place spaghetti squash, flesh down, onto the cookie sheet. Cook for about 30 minutes.
In a pot, boil 4 cups of water. Score and remove the core of the tomatoes. When water is boiling, lower in the tomatoes, one by one. Leave in for 30 seconds, then remove. Transfer from water to a plate using a strainer. Peel the skin off the tomato.
In a pan, heat 1/4 cup oil. Once heated, add garlic and simmer for 10-15 minutes, stirring occasionally, to ensure to burning. Add the cooked and peeled tomatoes to the oil and garlic. Smash tomatoes using a potato smasher till mushy and saucy. Add chopped basil. Cook no longer than 45 minutes on low heat. Season with salt and pepper to taste.
Remove squash from oven. Using a fork, scratch the flesh seperating from the skin to create the spaghetti, into a bowl.
Add spaghetti squash into the pan with the sauce. On low heat, mix together. Season with salt and pepper to taste.
Transfer back to the bowl and top with parmesan cheese. Serve.