- 2 Delicata squashes, seeds removed, cut into 1-inch rounds
- 2 tablespoons olive oil
- Kosher salt, freshly ground pepper
- 2 Fresno chiles, thinly sliced
- ¾ cup red wine vinegar
- ¼ cup honey
- 2 tablespoons golden raisins, chopped
- 1 teaspoon crushed red pepper flakes
- Preheat oven to 400°. Place kabocha and delicata squash on separate large rimmed baking sheets. Drizzle with oil; season with salt and pepper. Roast, tossing occasionally, until squashes are golden brown and tender, 30–35 minutes for kabocha and 20–25 minutes for delicata.
- Meanwhile, bring chiles, vinegar, honey, raisins, red pepper flakes, and a pinch of salt to a boil in a small saucepan over medium heat. Reduce heat and simmer until syrupy, 8–10 minutes.
- Brush half of warm agrodolce over warm squash. Transfer to a platter.
- Just before serving, reheat remaining agrodolce, adding a splash of water if needed to loosen. Spoon over squash.
Do Ahead: Dish can be made 3 hours ahead. Store tightly wrapped at room temperature.