Preheat the oven to 350°F (175°C).
Heat olive oil in a large oven-safe pot or Dutch oven over medium-high heat.
Add the beef cubes and brown on all sides, about 5-7 minutes. Remove the beef and set aside.
In the same pot, add the chopped onion and sauté until translucent, about 5 minutes.
Add the minced garlic and cook for 1 minute until fragrant.
Return the beef to the pot and stir in the crushed tomatoes, tomato sauce, and red wine.
Add the beef broth, dried oregano, dried thyme, ground cinnamon, ground allspice, salt, and black pepper. Stir to combine.
Bring the mixture to a boil, then reduce heat to low and simmer uncovered for 1 hour, stirring occasionally.
After 1 hour, stir in the orzo pasta, making sure it is evenly distributed in the sauce.
Cover the pot with a lid and transfer it to the preheated oven.
Bake for 40 minutes, or until the orzo is tender and most of the liquid is absorbed.
Remove the pot from the oven and sprinkle the grated kefalotyri cheese evenly over the top.
Return the pot to the oven and bake uncovered for an additional 5 minutes, or until the cheese is melted and slightly golden.
Remove from the oven and let rest for 5 minutes.
Garnish with chopped fresh parsley before serving.