- Adjust oven rack to middle position and heat oven to 400 degrees. Toss squash wedges, 2 tablespoons oil, 1 teaspoon salt, and 1 teaspoon pepper together in bowl until thoroughly coated. Arrange wedges on rimmed baking sheet with 1 narrow cut side down. Roast until browned on first side, about 20 minutes. Flip wedges so other narrow cut side is down and continue to roast until browned on second side and tip of paring knife slips easily into flesh, about 15 minutes longer.
- Remove sheet from oven and let wedges cool slightly. Once cool enough to handle, scoop flesh from 2 least attractive wedges into bowl; discard skins. (You should have about 3/4 cup of scooped squash.) Turn remaining 6 wedges skin side down on sheet.
- Heat 1 tablespoon oil in 12-inch nonstick skillet over medium heat until shimmering. Add kale, apple, and 1/4 teaspoon salt and cook, covered, until kale is wilted, about 3 minutes. Uncover and continue to cook until any liquid has evaporated, about 30 seconds. Stir in scooped squash, mashing with spoon to incorporate, and cook until beginning to brown, about 1 minute.
- Push squash mixture to sides of skillet. Add garlic, rosemary, and remaining 1 tablespoon oil to center of skillet and cook until fragrant, about 30 seconds. Stir garlic mixture into squash mixture. Stir in vinegar and cook until evaporated, about 1 minute. Off heat, stir in butter and season with salt and pepper to taste.
- Divide filling evenly among wedges on sheet. Evenly sprinkle goat cheese and almonds over filling. Bake until cheese is softened and squash heated through, 5 to 7 minutes. Drizzle with extra oil before serving.
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