Preheat oven to 375 degrees F.
Thoroughly wash the outside of the spaghetti squash to remove any dirt or grime. Using a sharp knife, cut the spaghetti squash in half from top to bottom. Be careful, as the skin is tough and hard to cut!
Drizzle the inside of each spaghetti squash with olive oil and season with salt and pepper. Place the squash cut side down on a baking sheet and cook in oven for 30-40 minutes. The squash is done when the inside can be easily pierced with a fork.
While the spaghetti squash is in the oven, drizzle a skillet with olive oil and place over medium-high heat. Add diced onions and garlic and saute until soft, then add ground beef. After the beef is cooked though, add the diced tomatoes, oregano, basil, red wine, salt and pepper. Set to low heat and let simmer.
When spaghetti squash is done, run a fork through the inside to separate the strands. Make a slight well in the center, and divide beef mixture evenly between the four halves. Place the spaghetti squash boats back in the oven for another 5-10 minutes.
Garnish with cheese, and enjoy!