Preheat oven to 200C/400F/Gas 6. Spray a large baking dish with non-stick cooking spray and set aside.
Place the acorn squash halves cut side up in the prepared baking dish and brush the cut edges with one tablespoon of olive oil. Season with salt and black pepper, to taste.
Place the baking dish on the center rack in the preheated oven and roast for 40 minutes, or until the squash is fork-tender.
In the meantime, heat the remaining olive oil in a large skillet over medium heat.
Add minced garlic and pancetta and cook, stirring occasionally, until slightly browned, approximately 2-3 minutes.
Add chopped mushrooms and cook, stirring occasionally, until they start to brown, approximately 4-5 minutes.
Add sliced onions and continue cooking, stirring once or twice, for another 3-4 minutes.
Stir green lentils, fresh sage, and red wine into the skillet. Cook, stirring occasionally, until mixture thickens, approximately 8-10 minutes.
Remove from heat and stir in the chopped dates and toasted walnuts. Season with salt and black pepper, to taste. Set aside.
When ready, remove the cooked squash from the oven and cool slightly before filling each half with the mushroom mixture. Sprinkle each half with some freshly grated Parmesan cheese.
Return stuffed squash to oven for another 5-10 minutes, or until heated through and the cheese starts to melt.
Remove from oven and serve immediately. Enjoy!