Preheat oven to 200°C (400°F). Line a baking sheet with parchment paper.
Brush acorn squash halves with olive oil and season with salt and pepper. Place cut-side down on the baking sheet.
Roast squash for 30 minutes until tender and lightly caramelized.
While squash roasts, heat olive oil in a skillet over medium heat.
Add chopped onion and sauté until soft. Add garlic and cook until fragrant.
Add ground pork and cook until browned, breaking it apart.
Stir in diced apple, sage, thyme, cinnamon, salt, and pepper.
Pour in chicken broth and simmer for 5 minutes until juicy and flavorful.
Remove squash from oven and turn cut-side up.
Spoon pork and apple filling evenly into each squash half.
Return to oven and bake for 15 minutes until everything is heated through.
Remove from oven, garnish, and serve.