Heat the oven to 425°F. Toss the diced squash with 1 tablespoon olive oil, salt, and pepper, then spread it on a sheet pan.
Roast until tender with browned edges, 20 to 25 minutes, stirring once. Let the squash cool until warm or room temperature.
Whisk the remaining olive oil with apple cider vinegar, maple syrup, and Dijon mustard until combined.
Arrange the greens in a serving bowl. Add the apple, cranberries, pecans, goat cheese, and squash.
Drizzle with dressing just before serving and toss gently.
