Preheat the oven to 400°F (200°C). Line baking sheet with parchment paper.
About an inch from the top of the drumstick, where the meat ends, make a circular cut around the bone, slicing through the meat and tendons. Use a sharp knife or kitchen scissors. Push the meat upwards towards the bone to create a lollipop shape.
In a mixing bowl, combine ketchup, sugar, soy sauce, Worcestershire sauce, vinegar, olive oil, minced garlic, and black pepper. Stir well until all the ingredients are fully mixed.
After preparing the drumsticks into lollipops, place them in a shallow dish or bowl with the bone facing down (upside down).
Pour the marinade over the chicken, making sure the exposed meat is fully coated. Marinate in the sauce for 1-3 hours. Set aside some of the sauce for basting later.
Transfer the marinated drumstick lollipops to a baking tray lined with parchment paper and bake.
Bake for 45 minutes, basting with the sweet sauce halfway through.
Once golden brown, remove the chicken lollipops from the oven and let them cool for a few minutes before serving. Garnish with sesame seeds, chopped green onions, or cilantro if desired.