Preheat oven to 400°F (200°C)
In a medium bowl, toss crumbled bacon with shredded cheddar cheese until evenly combined
Lightly coat a 12-cup muffin tin with cooking spray
Season ground beef evenly with kosher salt and freshly ground black pepper
Divide beef into equal portions and press each portion into the muffin cups
Press beef firmly up the sides to form a bowl shape
Spoon the bacon-and-cheese mixture evenly into each beef cup
Bake until beef is fully cooked and cheese is melted and bubbly
Remove from oven and allow to cool slightly
Use an offset spatula or knife to carefully release each burger bowl from the tin
Drizzle ranch dressing over the top
Sprinkle with chopped chives
Serve warm with bread and butter pickles on the side