Preheat and Prepare Tofu: Begin by setting your oven to 425°F (220°C). Slice the tofu into slabs about 1 inch thick. Pat the pieces thoroughly dry using paper towels, then arrange them in a single layer on a rimmed baking sheet. Cover the slabs with more paper towels and let them sit to remove excess moisture while you prepare the sauce.
Cook the Maple Syrup Sauce: In a small saucepan, combine the maple syrup, grated ginger, and chile powder. Heat the mixture until it thickens slightly and reduces by about one-third, which should take around 3 minutes. Stir in the olive oil once the mixture is ready.
Season and Roast the Squash: Place the squash cubes on another rimmed baking sheet. Sprinkle them generously with salt, pepper, and the chopped sage. Drizzle half of the prepared maple syrup mixture over the squash and toss well to coat. Spread the cubes out evenly and roast them in the oven, turning them occasionally, until they are golden brown and tender, about 45 minutes.
Flavor and Roast the Tofu: While the squash is roasting, mix the soy sauce and sherry vinegar into the remaining maple syrup mixture. Remove the paper towels from the tofu and sprinkle the pieces with a little salt. Brush the tofu with half of the soy-maple mixture and roast it for 20 minutes. Flip the tofu slabs, brush them with the remaining mixture, and continue roasting for an additional 15–20 minutes until golden and flavorful.
Assemble the Dish: Once the squash is cooked, toss it with the fresh cilantro or basil leaves. Arrange the squash and tofu together on a serving platter. Sprinkle the dish with sliced scallions for garnish and finish with an extra drizzle of sherry vinegar, if desired.