Italian Grilled Steak Sandwich

Total Time

Prep: 35 min. + marinating Grill: 15 min. + chilling


8 servings

Updated: Sep. 19, 2023
If you need to feed a hungry crowd, you can't go wrong with steak sandwiches. They're easy to make and rich with the flavors of Italy. —Gilda Lester, Millsboro, Delaware


  • 1/2 cup reduced-sodium teriyaki sauce
  • 2 tablespoons lemon juice
  • 2 tablespoons olive oil
  • 2 tablespoons Worcestershire sauce
  • 1 beef flank steak (1 pound)
  • 1 round loaf Italian bread (about 2 pounds), unsliced
  • 4 plum tomatoes, chopped
  • 4 green onions, thinly sliced
  • 1/4 cup Greek olives, coarsely chopped
  • 1/4 cup sliced pepperoni
  • 1 tablespoon thinly sliced fresh basil leaves
  • 2 tablespoons plus 1/4 cup prepared Italian salad dressing, divided
  • 2 cups fresh arugula


  1. Place first 4 ingredients in a large bowl or shallow dish. Add steak and turn to coat. Refrigerate, covered, 8 hours or overnight.
  2. Remove steak, discarding marinade. Grill steak, covered, over medium heat or broil 4 in. from heat until meat reaches desired doneness (for medium-rare, a thermometer should read 135°; medium, 140°), 6-8 minutes per side. Cool completely.
  3. Cut bread loaf horizontally in half. Hollow out both halves, leaving a 1/2-in. shell (save removed bread for another use). Cut steak across the grain into thin slices. In a bowl, toss tomatoes with green onions, olives, pepperoni, basil and 2 tablespoons dressing. In another bowl, toss arugula with remaining 1/4 cup dressing.
  4. Place half the arugula in bread bottom. Layer with steak, tomato mixture and remaining arugula; replace top. Wrap in foil; refrigerate at least 1 hour. Cut into wedges to serve.

Nutrition Facts

1 wedge: 260 calories, 10g fat (3g saturated fat), 30mg cholesterol, 567mg sodium, 24g carbohydrate (4g sugars, 2g fiber), 16g protein. Diabetic Exchanges: 2 lean meat, 1-1/2 starch, 1 fat.