Preheat oven to 350 degrees. Spray 9x5 loaf pan with cooking spray.
In a large mixing bowl, mix flour, sugar, baking powder, and baking soda together.
Combine oil, Greek yogurt, eggs, and vanilla in separate bowl. Stir into dry ingredients just until moistened.
Make the Cinnamon Swirl by mixing the 2/3 cup of sugar and cinnamon together in small bowl.
Pour 1/3 of the batter into the prepared loaf pan. Sprinkle 1/2 cup of strawberries over batter. Sprinkle 1/2 of the cinnamon sugar over strawberries.
Pour 1/3 of the batter over cinnamon sugar layer. Sprinkle 1/2 cup of strawberries over batter. Sprinkle the rest of the cinnamon sugar over top.
Pour the remaining batter over cinnamon sugar layer. Sprinkle remaining strawberries over final layer of batter.
Make crumble topping by mixing flour, sugar in small bowl. Cut in the butter using a fork until a crumble forms. Sprinkle crumble over bread batter.
Bake for 60 minute or until toothpick inserted comes out clean.
Whisk powdered sugar and milk together. Drizzle over cooled bread.