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In a large skillet over medium heat, cook the ground beef until evenly brown. Drain and set aside.
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Heat the oil in the skillet over medium heat. Mix in the squash, onion and garlic and sauté until tender.
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Add the ground beef and tomatoes (and water if fresh tomatoes are used) into the skillet. Season with chili powder, cumin, paprika, salt, and pepper.
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Turn mixture into an ovenproof casserole dish. Top with cheddar cheese. Bake in 400°F oven for 15 minutes.