Stir in the tomatoes and their juices, the wine and garlic; cover and cook for 10 minutes to create a chunky sauce, breaking up the tomatoes as they cook.
Heat the remaining tablespoon of oil in a separate medium skillet over medium heat. Once the oil shimmers, add the meat. Season with the remaining salt and pepper. Cook for 15 minutes, using a wooden spoon to break up clumps. The meat should be completely browned. Stir into the sauce until well incorporated and heated through.
Scoop out the squash seeds; discard or reserve for another use. Use a fork (or two) to shred the squash flesh, dragging the fork through lengthwise. Transfer the resulting strands to a mixing bowl or serving platter. Discard the empty skins.
Spoon the sauce over the squash and toss to incorporate, or spoon evenly over the squash. Garnish with a sprinkling of the cheese, if desired. Serve right away.
NUTRITION Per serving: 300 calories, 17 g protein, 18 g carbohydrates, 13 g