Preheat the oven to 400 degrees F (200 degrees C). Line a rimmed baking sheet with aluminum foil.
Trim and clean Brussels sprouts; halve any large ones. Transfer to a large bowl.
Add bacon, salt, and pepper; dizzle in oil and syrup. Toss until well coated.
Transfer to the prepared baking sheet in a single layer.
Roast in the preheated oven until bacon is crispy and Brussels sprouts are caramelized, 20 to 30 minutes, stirring halfway through.
