Heat oven to 400 degrees F. Line a baking sheet with a silicone mat or parchment paper.
Rinse Brussels sprouts, remove outer leaves, and cut off stems. If using large sprouts, cut into quarters. If using smaller sprouts, cut in half. Place in a large bowl.
To the sprouts, add oil, melted butter, vinegar, brown sugar, garlic powder, onion powder, salt, and pepper. Mix until sprouts are coated.
Pour sprouts onto prepared baking sheet leaving some room to one side. In the space left on the baking sheet, lay out bacon strips.
Bake for 25 to 30 minutes until bacon is crispy and sprouts are cooked and slightly browned.
Remove from oven. Transfer Brussels sprouts to a serving bowl and bacon to a cutting board. Chop bacon. Add dates, apples, and bacon to sprouts and stir to combine.
Serve immediately. You can drizzle on some balsamic glaze if you like.