Position a rack into the center position of the oven and preheat oven to 400F. Line a baking sheet with parchment paper.
Spread acorn squash cubes onto prepared baking sheet and toss with 2 tablespoons Secolari Sevillano Olive Oil. Mix cinnamon, onion powder, cumin, 1/2 teaspoon salt, and 1/4 teaspoon black pepper in a small bowl; sprinkle spice mixture over squash cubes.
Bake on the center rack of preheated oven until squash are tender, 15 to 20 minutes. Drizzle one tablespoon of olive oil, mix, and rmove from oven and allow to cool completely.
Whisk apple cider vinegar, maple syrup, Secolari Chardonnay Mustard, orange zest, garlic, 1/2 teaspoon salt, and 1/2 teaspoon black pepper in a bowl until thoroughly combined; slowly drizzle olive oil into vinegar mixture, whisking constantly, until olive oil incorporates into the dressing. Refrigerate while completing remaining steps.
Toss cooked acorn squash cubes, baby arugula, cranberries, pistachios, and goat cheese in a salad bowl; drizzle with dressing serve.