Heat the olive oil in a large nonstick skillet over medium-high heat. Add onion, carrot, celery, dried oregano, and minced garlic; sauté for 2 minutes.
Combine onion mixture, ½ cup ketchup, beef, bread crumbs, mustard, Worcestershire sauce, pepper, and eggs, and the remaining ingredients in a large bowl. I found that it was easiest to just use my hands to make sure that all the ingredients were completely incorporated.
Spoon the meat mixture into 12 muffin cups coated with cooking spray- each cup will be filled to the top. Top each meatloaf with about 1-2 teaspoons ketchup.
Bake at 350℉ for 25 minutes or until a thermometer registers 160℉.
Let the cupcakes cool. In the meantime, put the mashed potatoes into a pastry bag (or a ziploc bag with the corner cut off) with a wide star tip or circular tip and pipe the mashed potatoes on top of the meatloaf.
Sprinkle with bacon bits and green onions.
Notes
You can make whatever type of mashed potatoes you’d like for these delicious meatloaf cupcakes. I promise that you will want some delicious mashed potatoes to finish off these cupcakes.