Preheat oven to 375 degrees. Make the crust: Roll out pate brisee to a 1/8-inch thickness on a lightly floured surface. Fit dough into a 9-inch pie plate, and trim crust to a 1-inch overhang. Fold edges under, and crimp as desired. Freeze until firm, about 30 minutes.
Meanwhile, make the filling: Drizzle pumpkin and squash wedges with olive oil, and roast on a rimmed baking sheet until tender (times will vary).
Line crust with parchment, leaving an overhang on all sides. Fill with pie weights or dried beans. Bake until edges of crust begin to turn golden, about 20 minutes. Remove from oven, and remove weights and parchment. Bake until golden brown, 15 to 20 minutes more. Let cool on a wire rack.
Peel pumpkin and squash, and transfer flesh to a food processor. Puree until smooth.
Reduce oven temperature to 325 degrees. Whisk pumpkin and squash puree, eggs, egg yolks, heavy cream, sugar, brandy, sage, cinnamon, ginger, allspice, cloves, nutmeg, 3/4 teaspoon salt, and 1/8 teaspoon pepper in a bowl.
Pour filling into pie shell, and smooth top using an offset spatula. Bake until just set but still slightly wobbly in the center, about 1 hour (filling will continue to set as it cools). Let cool on a wire rack. Serve slightly warm, at room temperature, or chilled, with whipped cream.
Pie can be refrigerated up to 3 days.
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