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Choose Brussels sprouts that are similar in size to ensure even cooking. To keep the sprouts’ leaves intact, be sure to trim just a small amount from of the stem before halving the sprouts.
Adjust oven rack to lowest position and heat oven to 475 degrees. Spray rimmed baking sheet with vegetable oil spray. Toss sprouts and 1 tablespoon oil together in large bowl and set aside. Toss onion and remaining 1 tablespoon oil together in small bowl. Arrange onion in even layer on half of prepared sheet. Arrange bacon in even layer on other half of sheet. Cook until bacon begins to brown and onion begins to soften, 7 to 9 minutes.
Remove sheet from oven and transfer to wire rack. Add sprouts to sheet and stir to combine bacon, onion, and sprouts. Flip sprouts cut side down and nestle into sheet. Return sheet to oven and continue to cook until sprouts are deep golden brown and bacon is crispy, 15 to 17 minutes longer. Sprinkle with salt and pepper. Transfer to platter and serve.