Preheat oven to 400 degrees F. Spray a sheet pan with cooking spray.
In a large bowl, combine the squash, 1/2 tablespoon oil, 1/4 teaspoon salt and pepper, to taste. Toss to coat. In another large bowl, combine the Brussels sprouts, remaining tablespoon of oil, 1/4 teaspoon of salt and pepper, to taste.
Spread the vegetables in an even layer on 1 sheet pan. Top with bacon. Roast for 20 minutes, with a spatula, toss veggies and roast an additional 15 minutes.
Meanwhile, in a small sauce pot, combine the syrup and soy sauce. Over medium low heat, simmer sauce for 5 minutes, or until it begins to thicken slightly. Set aside.
When vegetables are done roasting, transfer to a serving dish. Add maple soy sauce and toss to coat.