Preheat oven to 400°F (200°C).

Prepare a sheet pan lined with foil, and lightly spray with cooking spray. Place butternut squash (with seeds removed) on pan, and bake 30 minutes or until soft.

Puree squash with milk in blender until smooth then set aside.

In a bowl, toss garlic, beans, cumin, oregano, salt, and pepper.

Heat oil in the pan over medium heat. Once hot, add the bean mixture to the pan. Cook for 1 to 2 minutes. Add half of the reserved bean liquid. Allow to cook and mash about half the beans until slightly thickened, about 8 minutes. Remove from heat and stir in cilantro.

Lay corn tortillas on flat surface then top with 1/4 cup of butternut squash puree and 1/4-1/2 cup of cannellini bean mixture.

Sprinkle top of mixture with 1 tablespoon of cheese, then top with another corn tortilla and press gently.

Heat a large skillet over medium heat and coat with pan spray. Place quesadillas in the skillet one at a time, working in batches if needed. Cook each side for about 3 minutes, until goldren brown. Before flipping the quesadillas, spray the tops with pan spray to ensure both sides brown evenly.

Alternate Cooking Method: Arrange quesadillas in a single layer on a baking sheet. Bake in the oven until cheese is melted and edges are crisp, flipping half way through, about 8-12 minutes.