Preheat your oven to 350°F and line a baking sheet with parchment paper.
In a large skillet over medium-high heat, cook the ground beef along with the sliced onions and bell peppers. Sauté until the vegetables are tender and the beef is fully browned, stirring occasionally to ensure even cooking.
Once the meat mixture is cooked through, carefully drain off any excess grease to avoid sogginess in your rolls.
Stir in the Worcestershire sauce and cream cheese, then season with salt and pepper. Continue to mix until the cream cheese is fully melted and the mixture becomes smooth and cohesive.
On the prepared baking sheet, form eight evenly sized mounds of shredded Monterey Jack cheese, spacing them apart. Flatten them slightly to form circles.
Place the baking sheet in the oven and bake for 8 to 10 minutes, or until the cheese circles have melted and the edges begin to crisp and turn golden-brown with a lacy texture.
Allow the cheese circles to cool just slightly—enough to handle but still pliable. Spoon a portion of the beef and vegetable filling onto each cheese circle, then gently roll them up to enclose the filling.
Let the roll-ups sit for a few minutes to firm up before serving warm.