Kabocha Squash Pie with Spiced Crust

Name: Kabocha Squash Pie with Spiced Crust
Ingredients: 1 small to medium kabocha squash, cut into sixths, seeds removed; Olive oil; 1 1/2 cups all-purpose flour, plus more for bench flour; 1/4 cup sugar; 1 teaspoon ground cinnamon; 1/2 teaspoon allspice; 1/2 teaspoon ground ginger; 2 grates fresh nutmeg; Pinch kosher salt; 1 1/2 sticks cold butter, cut into pea-size pieces; 1 egg yolk; 2 to 3 teaspoons ice cold water; 4 large eggs; 3/4 cup heavy cream; 3/4 cup sweetened condensed milk; 1/2 cup light brown sugar; 1/4 cup bourbon, optional; 1 teaspoon vanilla extract; Heavy cream, for garnish; Pinch cinnamon, for garning