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Butterfly the tenderloin: Slice the pork lengthwise down the center, leaving the roast attached by about 1 inch. Open the pork like a book, cover with plastic wrap, and, using a meat mallet or rolling pin, pound to an even ½-inch thickness. Season with salt and black pepper, then cover one side of the pork with the prosciutto and Parmigiano-Reggiano. Starting at one of the long ends, tightly roll up the meat into a log, then tie securely with butcher’s twine.
To a large skillet over medium heat, add the oil and butter. When the butter is melted, add the garlic and rosemary and cook until the garlic is golden, 1–2 minutes. Place the pork in the skillet and sear on all sides until evenly browned, about 8 minutes. Add the lambrusco and marsala, scraping up any browned bits. Cook, turning the roast once halfway through, until the sauce reduces by about a third and the surface of the meat is deep red, 18–20 minutes. Transfer the pork to a plate.
Add the cream to the skillet, turn the heat to medium-high, and cook, whisking occasionally, until the sauce has thickened slightly, about 15 minutes. Remove from the heat and season to taste with salt and black pepper. Remove the twine, slice the pork, drizzle with the sauce, and serve hot.