Best 9 Olive Stuffed Flank Steak Recipes

STUFFED FLANK STEAK

Steps:

• Preheat oven to 350 degrees F (175 degrees C).
• In a medium bowl, combine the stuffing mix, water and butter or margarine. Mix well and let stand for 5 minutes. Spoon the stuffing onto the steak, leaving a 1 inch border. Add the green onions and the red bell pepper.
• Roll from the long edge of the steak and secure with wooden toothpicks. Place steak seam side down in a 9x13 inch baking dish.
• In a separate small bowl, combine the gravy, wine OR apple juice, garlic and cheese. Mix well and pour over the steak.
• Bake at 350 degrees F (175 degrees C) for 1 hour, remove from oven and let stand before slicing.

STUFFED FLANK STEAK IN THE OVEN

Steps:

• Place flank steak in the freezer for 20 minutes.
• Meanwhile, heat 1 tablespoon olive oil in a skillet. Add mushrooms, celery, sun-dried tomatoes, and garlic; saute until softened, about 5 minutes. Remove from the heat and place in a large bowl.
• Pat roasted red peppers dry. Chop and add to the vegetable mixture. Add bread crumbs, parsley, 2 tablespoons olive oil, capers, salt, pepper flakes, and black pepper. Mix to combine.
• Preheat the oven to 425 degrees F (220 degrees C).
• Remove steak from the freezer and season with salt and pepper. Turn the long side of the steak towards you and place on a flat work surface. Slice horizontally through the middle to within 1/2 inch of the opposite edge, being careful not to cut all the way through to the other side. Open the 2 sides and spread them out like an open book.
• Leaving a 1-inch border around the edges, layer prosciutto and provolone cheese over the entire steak. Top with bread crumb mixture, patting down to adhere. Roll steak up tightly starting at the small end. Use kitchen twine to tie steak in 1-inch increments taking care to tie tightly at both ends. Season with more salt and pepper and brush with remaining 2 tablespoons olive oil. Place steak carefully on a broiler pan.
• Bake in the preheated oven until an instant-read thermometer inserted into the center reads 145 degrees F (63 degrees C) for medium-rare, 160 degrees F (71 degrees C) for medium, or 170 degrees F (77 degrees C) for well done, 35 to 40 minutes. Turn on the broiler and broil for an additional 10 minutes.
• Remove from the oven and let stand for 10 minutes before slicing and serving.

OLIVE-STUFFED FLANK STEAK

Steps:

• To make the stuffing: Heat 2 tablespoons oil in a medium sauté pan over medium heat. Add the onion and cook, stirring occasionally, until soft and caramelized, about 10 minutes. Add the garlic, and cook until aromatic, a few minutes more. Remove from the heat, and transfer to a bowl. Stir in the olives, herbs, pine nuts, and currants. Set aside to cool.
• To prepare the flank steaks for stuffing; place one of the steaks on a work surface, cover it loosely with a piece of plastic wrap, and use a meat pounder to pound the steak until about 1/3 inch thick. Using a sharp knife, score the steak in a crisscross pattern, making 3 to 4 shallow cuts in each direction, being sure not to cut all the way through. Turn the steak over, and spread half the stuffing evenly over the unscored surface of the steak. Roll up the steak lengthwise, like a jelly roll. Using kitchen twine, tightly tie the steak to keep it securely rolled up. Season with salt and pepper. Repeat with the remaining steak and stuffing.
• Preheat the oven to 400 degrees. Pour about 2 tablespoons of oil into a large roasting pan. Place over two burners over medium-high heat. When the oil is hot, add the steaks and sear on all sides, turning with tongs, until browned, 6 to 8 minutes. Remove steaks from pan, transfer to a plate, and set aside. Discard any fat in the pan and scrape out and discard any burned bits that may have escaped from the stuffing. Return the steaks to the pan, place in the oven, and roast, uncovered, for 7 to 8 minutes. Turn the steaks, and continue to roast until the internal temperature of the steaks reads between 120 degrees.and 130 degrees.on an instant-read thermometer, about 8 minutes.
• Remove pan from oven and allow the steaks to rest for 5 to 8 minutes. Cut, and remove the twine. Transfer steaks to a cutting board. Using a sharp knife, cut them into slices 1/2 to 3/4 inch. Arrange the slices on a platter, and pour any accumulated pan juices over the top. Serve with tomato confit.

ANTIPASTI-STUFFED FLANK STEAK

Steps:

• For the flank steak: Set the flank steak on a cutting board. Starting at the thin, narrow end of the steak, slice it in half horizontally to within 2 inches of the opposite wide end. Open it up like a book so you have one long piece. Pound the steak with a mallet to an even thickness of about 1/2 inch.
• Whisk together the oil, vinegar, honey, red pepper, garlic and 1/2 teaspoon each salt and pepper in a medium bowl. Combine the marinade with the meat in a large resealable plastic bag and flip over several times to make sure the meat is well coated. Marinate in the refrigerator for 2 hours, flipping several times.
• For the herb paste and sauce: Combine the basil, parsley, red pepper, garlic and 1 teaspoon salt in a food processor and pulse until finely chopped. With the motor running, slowly pour in 1/4 cup of the oil. Remove 2 tablespoons of the herb paste from the processor and mix with the remaining 1/4 cup oil in a small bowl; reserve this sauce for finishing.
• Prepare an outdoor grill for direct and indirect grilling. (If your grill has a thermometer, aim to keep the temperature at about 350 degrees F throughout grilling.)
• Remove the steak from the marinade and pat dry. Spread it flat on a work surface. Cover the steak with the remaining herb paste, leaving a 1-inch border along the edges. Layer with the ham, mozzarella and salami, then sprinkle with the mushrooms and roasted peppers. Arrange the hot peppers in a line along the edge of one of the short ends (when you roll up the steak they will be in the middle). Roll up the steak like a jelly roll, starting at the short end with the hot peppers. Tie the roll closed around the circumference with butcher's twine at 2-inch intervals. Tie one more piece of twine lengthwise around the meat.
• Put the steak on the direct heat side of the grill and cook, turning, to brown all 4 sides, about 2 minutes per side. Move the steak to the indirect heat side of the grill, cover and cook, turning occasionally, until the very center reads 115 degrees F on an instant-read thermometer for a steak that is well done on the outside and medium rare in the center, 25 to 30 minutes more. (Test frequently; the time will vary based on the temperature of your grill.) Let the steak rest 5 to 6 minutes.
• Untie the steak and cut it into 6 thick slices. Serve with the reserved herb sauce for drizzling.

GRILLED STUFFED FLANK STEAK

Steps:

• In a small bowl, combine garlic, shallot, parsley, sage, and olive oil. Set aside. Lay out two long pieces of plastic wrap side by side and place flank steak on plastic wrap. Butterfly cut steak. (Lay flank stake out flat and slice in half horizontal, from side to side, stopping before you get to the edge. Open it up and your steak will suddenly be twice as the size). Ask your butcher or store butcher to do this to save you time! Place two more pieces of plastic wrap on top of steak. Pound flank steak into rough rectangle with a meat hammer or gently with a clean nail hammer so as to not pound a hole in it . Remove top plastic wrap. Spread garlic and herb oil over steak. Top with prosciutto. Place provolone on top of prosciutto, leaving a boarder around steak without cheese. Like cinnamon rolls, working with the wide end, roll up steak into a pinwheel. Cut 12 (8 inch) pieces of string. Tie up each end of steak roll. Then use the remaining string to tie up the steak into 1 inch pieces, working from outside edges to inside. Once steak is tied up, then roll log so that the seam is facing you. Place a skewer between each of the strings and on each end, making sure to skewer the edges to secure them. Slice the steak between the skewers and snip off the strings. Salt and pepper each side of the pinwheels. Cook on a preheated and oiled grill for approximately 4 - 5 minutes per side, depending on how done you want your steaks. You can also cook these on foil or a grilling mat. Once cooked, remove from grill, and let sit for 3 - 5 minutes. You can cover them with foil if you wish. Remove the skewers and devour!

GRILLED FLANK STEAK WITH OLIVE AND HERB SAUCE

Steps:

• Let steaks sit at room temperature 1 hour. Heat grill to medium-high. Pat steaks dry. Brush with 2 tablespoons oil, and season liberally with salt and pepper. Grill 7 to 8 minutes per side (or until internal temperature reaches 135 degrees) for medium-rare. Let steaks rest, loosely tented with foil, 10 minutes.
• Meanwhile, mix together olives, peperoncini and their juice, parsley leaves and stems, oregano, and remaining 2/3 cup oil. Sauce can be made 1 day in advance and refrigerated; bring to room temperature before serving.
• Thinly slice steaks against the grain; arrange on a platter. Spoon half the sauce on top; serve remaining sauce on the side.

MEDITERRANEAN INSPIRED STUFFED AND ROLLED FLANK STEAK

Steps:

• Combine all the stuffing ingredients in a food processor and process until they form a smooth paste, about 45 to 60 seconds.
• Prepare the flank steak by placing between plastic and pounding to a thickness of 1/3 inch; score on one side in a criss-cross pattern.
• Turn steak over and season well with salt and pepper.
• Smooth all but 1 tablespoon of the stuffing over the entire steak; reserved stuffing will be used later in a sauce.
• Roll steak up and tie with kitchen twine in about 3 places.
• Place the steak, uncovered, in the refrigerator for at least two hours up to overnight (you want the outside to dry a bit and the inside to marinate).
• Preheat oven to 375 degrees F and bring the steak to room temperature.
• Heat a large skillet over medium high heat; season steak on all sides generously with salt and pepper and sear well, in a little oil, on all sides.
• Meanwhile combine reserved stuffing, water, mustard, garlic, rosemary, and oils in a roasting pan or baking dish; place a rack for the meat on top.
• Place meat on rack, brush with pan juices, and roast to an internal temperature of 120 degrees F, about 15 minutes.
• Let rest about 15 minutes, then slice into 1/4 inch slices; drizzle with pan sauce and more extra virgin olive oil if desired.

VEGETABLE-STUFFED FLANK STEAK

Steps:

• Cut steak horizontally from a long side to within 1/2 in. of opposite side. Open steak so it lies flat; cover with plastic wrap. Flatten to 1/4-in. thickness. Remove plastic; sprinkle steak with 1/8 teaspoon salt and pepper. Set aside. In a skillet, cook bacon until crisp. Remove to paper towels. Drain, reserving 2 tablespoons drippings., In the drippings, saute leeks, yellow peppers and 1 cup celery until tender. Stir in spinach, thyme, basil and bacon. Spoon over meat to within 1/2 in. of edges. Roll up tightly jelly-roll style, starting with a long side. Tie with kitchen string., Rub steak with garlic and remaining salt. In a large skillet, brown meat in oil on all sides. Place in a greased shallow roasting pan. Add onion and remaining celery. Combine remaining ingredients; pour over steak. Cover loosely with foil., Bake at 350° for 1 hour. Baste with drippings. Bake, uncovered, 15 minutes longer or until meat is tender. Let stand for 10-15 minutes. Remove string and slice. Discard bay leaf; thicken juices if desired.

FLANK STEAK WITH JALAPENO & OLIVE TAPENADE

Steps:

• Preheat barbecue to high heat.
• Brush grill with medium coat of oil.(Charcoal grills-before heating/gas grills- after heating.).
• Rinse olives and drain well.
• Mix olives, garlic, parsley, rosemary, and olive oil in blender or food processor until mixture forms a fine paste.
• Separate 1/2 cup to spread on steak.
• Rinse flank steak and pat dry.
• With tip of sharp knife, make shallow diagonal cuts about 1 inch apart on one side of the steak. Then make perpendicular cuts over the first ones to make a diamond pattern.
• Repeat cuts on reverse side of steak.
• Spread 1/2 cup of the olive tapenade paste over both sides of the steak, coating evenly.
• Place on grill; close lid.
• Cook until browned, 8-10 minutes.
• Turn steak and continue to cook until desired doneness. (about 2 minutes for rare, 4 minutes for medium-rare.).
• Remove to clean platter; let reast 5 minutes.
• Cut in thin, slanting slices across the grain.
• Serve.
• Extra tapenade that was not used on steak can be served on the side on toasted baguettes or mix with softened cream cheese for a delicious veggie dip.