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Preheat oven to 400°F. Place squash in a large rimmed baking pan and toss with 1 tablespoon oil and 1/4 teaspoon salt. Roast for 30 minutes. Set aside.
Heat the remaining 1 tablespoon oil in a large pot over medium-high heat. Add onions, peppers and garlic. Cook 8 minutes, stirring occasionally. Add tomatoes, chili powder, cinnamon, sugar, allspice and the remaining 1/2 teaspoon salt. Simmer 15 minutes over medium-low heat, with lid ajar. Stir occasionally.
Stir in cooked squash and beans. Simmer 5 minutes.
Serve chili over cooked spaghetti. Scatter cheese, crackers and scallions over the top.