Prepare the Tomato Sauce: Heat 1 tablespoon of olive oil over medium-high heat in a nonstick saucepan. Add crushed garlic and sauté for about 1 minute until fragrant. Stir in crushed red pepper flakes, cooking for an additional minute before adding plum tomatoes. Simmer for 15-20 minutes until thick, then stir in fresh basil and cool.

Cook the Filling: Heat a nonstick skillet over medium heat and cook spicy chicken sausage for 4-5 minutes, breaking apart until fully cooked. Drain grease, then combine sausage with Canadian bacon and mozzarella. Fold in ¼ cup of cooled tomato sauce and set aside.

Preheat the Oven: Preheat oven to 350°F (175°C) to ensure proper baking.

Assemble the Calzones: Layer three sheets of phyllo on a clean surface, spraying each layer with olive oil. Place filling in the bottom corner, fold over into a triangle, and press edges to seal. Cut small slits in tops for steam release.

Bake the Calzones: Arrange calzones on a wire rack over a baking sheet, spray tops with olive oil, and bake for 35-40 minutes until golden brown and crispy.

Serve and Enjoy: Let calzones rest for 5 minutes, serve warm with remaining tomato sauce, and enjoy!