Heat the oven to 375°F. Line a rimmed baking sheet with foil and set an oven-safe rack over it.
Pat the drumsticks dry. Season with the garlic powder, paprika, salt and pepper, then wrap each with a slice of thin-cut bacon, tucking the end underneath. Space them on the rack.
Roast for about 40–55 minutes, turning once, until the chicken reaches 165°F away from the bone and the bacon is cooked. If needed, briefly broil the cooked drumsticks to crisp the bacon, watching closely.
While the chicken cooks, toss the panko with the olive oil in a small skillet and toast over medium heat for 2–3 minutes, stirring, until lightly golden. Keep this topping separate from the raw chicken.
Sprinkle the cooked drumsticks with cheddar and the toasted panko. Return to the oven for 3–5 minutes to melt the cheese, then rest for 5 minutes before serving.