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Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper to prevent sticking and make cleanup easier.
Heat a skillet over medium-high heat. Add ground beef to the hot skillet and begin breaking it apart with a spatula. Once beef begins to brown, add the sliced onions and bell peppers. Cook until the beef is fully browned and vegetables have softened (about 5-7 minutes). Drain excess grease from the pan.
Return the skillet to medium heat. Add Worcestershire sauce, salt, and pepper to the beef mixture and stir to combine. Add cream cheese to the skillet and stir continuously until completely melted and incorporated. Remove the skillet from heat and set aside.
On your parchment-lined baking sheet, create 8 evenly spaced circles using the shredded Monterey Jack cheese, about ¼ cup per circle. Bake for 8-10 minutes until edges turn golden brown and cheese develops a lace-like appearance.
Remove cheese circles from the oven and let cool for about 1 minute. Place approximately 2 tablespoons of the beef mixture onto each cheese circle. Carefully roll or fold the cheese around the filling, creating a roll-up shape. Allow to cool for 2-3 minutes to set the shape as the cheese hardens.