Preheat the oven to 425°F (218°C) for a conventional oven (without fan). If using a convection oven (with fan), preheat to 400°F (204°C).
Delicata preparation:Trim off the ends, then scrub the squash clean. Pat dry and slice crosswise into ½-inch (1.27 cm) thick rings. Use a small teaspoon to scoop out the seeds and stringy parts.
Season: In a large mixing bowl, toss the squash with salt, pepper, cinnamon, and olive oil until evenly coated.
Roast: Line a large baking sheet with parchment paper. Spread the squash in a single layer. Bake on the middle rack at 425°F (conventional oven) for 20 minutes. Flip the rings and continue roasting for another 8–10 minutes, checking at the 8-minute mark. If using a convection oven (fan setting), set to 400°F and start checking a few minutes earlier. The squash is ready when golden brown on the edges and tender in the center.
Sauce & greens: Meanwhile, prepare the sauce in a small bowl. Cover and refrigerate until ready to serve. In another mixing bowl, toss the arugula with a pinch of salt and pepper, plus a drizzle of olive oil and lemon juice.
Combine & serve: Arrange the arugula on a large serving platter. Place the roasted squash on top. Sprinkle with cranberries and raisins, if using. Drizzle lightly with the sauce or serve it on the side. Enjoy warm or at room temperature.
Notes
Cutting size: In my testing, ½-inch (1.27 cm) slices are the sweet spot. They’re tender but still hold their shape, and the size works beautifully with the delicate toppings like arugula and cranberries.
Topping ideas: Swap the cranberries for toasted walnuts, almonds, or pistachios. Chop the nuts before adding.
Storage: Delicata squash has tender skin and doesn’t keep as long as other winter squashes. Once cooked, store in an airtight container in the fridge and eat within 3 days.
Reheating: Warm in a 400°F (204°C) oven for 10–15 minutes.
About the sauce: Mayo gives creaminess while yogurt adds tang. If you’d like to skip mayo, replace both with Greek yogurt for a thicker consistency. Add a touch of maple syrup if you’d like to balance the acidity.