Preheat the oven to 425 degrees F. Toss the squash, 1 tablespoon olive oil, the allspice, cayenne, 1/2 teaspoon salt, and black pepper to taste in a shallow baking dish. Roast until tender, stirring once, 15 to 20 minutes. Let cool slightly.
Whisk the yogurt, lime juice, 1 tablespoon water, the remaining 1 tablespoon olive oil and a pinch of salt in a bowl. Transfer the squash to a serving dish and drizzle with the yogurt dressing. Sprinkle with the pomegranate seeds and cilantro. Season with salt.