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Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper.
Heat a skillet over medium-high heat. Add ground beef and break it apart with a spatula. Once browned, add sliced onions and bell peppers. Cook until beef is fully browned and vegetables have softened (about 5-7 minutes). Drain excess grease.
Return the skillet to medium heat. Add Worcestershire sauce, salt, and pepper to the beef mixture. Stir to combine. Add cream cheese and stir until melted and incorporated. Remove from heat.
On the 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.
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. Roll or fold the cheese around the filling to create a roll-up shape. Allow to cool for 2-3 minutes to set.