Prep. Preheat oven to 425°F/220°C. Use a vegetable peeler to peel the whole squash then cut it into 1-inch cubes.
Season and roast squash. Toss the cubed squash with olive oil and spices then arrange into a single layer on a rimmed baking sheet or baking tray. Bake for 30-35 minutes or until fork tender, stirring halfway through.
Soak the cashews. Soak the cashews in a small bowl of boiling water for 10 minutes. Set aside.
Make the creamy base. Drain and rinse the cashews then add them to the base of a high-powered blender with fresh water, kosher salt, smoked paprika, ground cumin, garlic powder, black pepper, and red wine vinegar. Blend on high until completely smooth. Season to taste with more salt or vinegar as needed.
Make the fried sage leaves. Heat a bit of olive oil in a small saucepan over medium heat. Once hot, add the sage leaves and cook until crispy then remove from the pan and transfer to a paper towel to remove the excess oil. They're done when they stop sizzling.
Assemble. Pour the smoky cashew cream onto the bottom of a serving bowl then add the roasted squash on top. Add a drizzle of olive oil and top with fried sage leaves. Serve with pita chips, crackers, toasted bread, etc.