Preheat oven to 375°F. Brush 8 cups of a standard-sized muffin pan with 1 teaspoon oil. In large bowl, combine the meat, 1/4 cup ketchup, breadcrumbs, eggs, and cheese. Divide mixture into 8 small loaves and press into oiled cups. Evenly brush 1 Tablespoon ketchup on meatloaves. Bake until meatloaves reach an internal temperature of 165°F, about 25 minutes. Let cool 5 minutes.
In a medium skillet, heat 2 teaspoons oil over medium-high heat. Add garlic and cook 30 seconds. Add broccolini and salt. Cook 4 minutes. Add 1/2 cup water. Cover and simmer over low until crisp-tender and still bright green, about 6 minutes. serve alongside meatloaves.