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Preheat oven to 350 degrees. Coat a 9-by-13-inch baking dish with cooking spray.
In a large skillet, heat oil over medium-high heat. Cook onion and garlic until onions are translucent and fragrant.
Add butternut squash, cook 5 minutes, then reduce heat to simmer and cook an additional 10 minutes or until squash is tender and lightly browned. Stir in black beans, cumin, salt and pepper.
Place half the tortillas on a plate, cover with a damp paper towel, and microwave 30 seconds or until pliable. Repeat with remaining tortillas.
Spread ¼ cup enchilada sauce evenly on bottom of baking dish. Spoon ¼ cup squash and bean mixture onto center of each tortilla and roll up. Place seam side down in baking dish.
Pour remaining enchilada sauce evenly over the top over tortillas. Spread cheese evenly over enchiladas and topped with black olives.
Bake 15 to 20 minutes until heated through and cheeses melted. Remove from oven and sprinkle with green onions.