Preheat your oven to 350°F.
In a skillet over medium heat, cook ground beef, onion, and bell pepper until the meat is browned and vegetables are softened.
Stir in Worcestershire sauce, cream cheese, salt, and pepper, and cook until the cream cheese is melted and the mixture is well combined.
Line a baking sheet with parchment paper and arrange the shredded Monterey Jack cheese into 8 even circles.
Bake the cheese rounds for 8–10 minutes until the edges turn golden and start to crisp.
Remove from the oven and let the cheese cool just until pliable.
Place a spoonful of the beef mixture on each cheese circle and carefully roll the cheese around the filling.
Allow the rolls to cool slightly so the cheese sets before serving.