Cut bacon in half crosswise, then in half length-wise. Wrap each piece of sweet potato with a piece of bacon, securing with a toothpick.
Place sweet potatoes on foil lined baking sheet. Drizzle with olive oil. Sprinkle with chili powder.
Bake for 20 minutes. Remove from oven and flip potato pieces over. Return to oven and bake for an additional 20-25 minutes until bacon is crispy and potatoes are browned. Drain on a paper towel-lined plate.
Serve warm with sour cream, ranch dressing, or guacamole.