Slice a butternut squash in half, scoop out the seeds (save for later to roast them if you want), and put in a baking dish flesh side up. Drizzle olive oil on top and sprinkle with salt and pepper.
Slice about ½" off a head of garlic (the pointy end), exposing the cloves, and leaving the skin on. Put the garlic in aluminum foil and drizzle with a couple of teaspoons of olive oil. Cover the garlic with the aluminum foil.
Put the garlic in the baking dish with the butternut squash. Roast both for 40 minutes at 400° until tender. Let sit until cool.
With a fork, mash roasted garlic into the vegan cream cheese. Spread on a tortilla.
Take the skin off the butternut squash and mash with a fork. Spread on the other tortilla. Put both tortillas with filling together.
Heat some olive oil in a pan and add quesadilla. Cook on medium heat until browned. Flip and cook other side until browned.