Cut the squash in half the long way (you would be slicing through the stem on the top). Scoop out the seeds and discard.
Slice the squash into thin half-moon pieces, about 1/4 inch thick.
Toss the delicata squash slices in a bowl with 2 teaspoons of olive oil and at least 1/2 teaspoon each of salt and pepper.
Line a large baking sheet with parchment paper. Place the delicata squash slice son the sheet in a single layer—making sure they aren't on top of each other.
Roast in the oven for 15 minutes.
While the squash is roasting, prep the dressing. Add all of the ingredients for the dressing in a small mason jar. Seal and shake.
Add all of the salad ingredients to a large platter. Top with roasted squash slices and drizzle on the apple cider vinaigrette. Toss and serve.