This moist and fruity Pineapple Upside Down Cake is made even more irresistible with the addition of caramelized pineapple and our Maraschino Cherries.  Simple and delicious, it’s no wonder it’s been a tried-and-true favorite for decades!


Makes 12 servings 1x 2x 4x
  • Pineapple Topping Ingredients
  • 4 tablespoons unsalted butter melted
  • 1/2 cup light brown sugar
  • 10 canned pineapple rings juice reserved
  • 10 Maraschino Cherries Without Stems drained plus more for serving
  • Cake ingredients
  • 4 tablespoons unsalted butter melted
  • 1/2 cup light brown sugar
  • 1/2 cup granulated sugar
  • 1 large egg
  • 2 teaspoons vanila extract
  • 1/2 cup whole milk
  • 2 tablespoons reserved pineapple juice
  • 1/2 cup Greek yogurt
  • 1.25 cup all-purpose flour
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon kosher salt
  • Whipped cream, for serving


  2. Preheat your oven to 350°F. 
  3. Make the topping: Add the melted butter to a greased 9-inch round cake pan and sprinkle the brown sugar over top. Place 7 pineapple slices, or however many will fit, into the pan and place a Mezzetta® Maraschino Cherry in the center of each pineapple ring and in all the spaces in between. Cut the remaining pineapple slices in half and line the sides of the cake pan. 
  4. In a large bowl, whisk together the melted butter and both sugars until smooth using an electric hand mixer. Add in the egg, vanilla extract, milk, reserved pineapple juice and Greek yogurt and mix until combined. 
  5. In a separate bowl, add the flour, baking soda, baking powder and salt and stir to combine.  
  6. Using the electric hand mixer, carefully add the flour mixture into the wet mixture a little bit at a time, mixing as you go until a thick batter is formed. 
  7. Pour the batter into the prepared cake pan and transfer to the oven to bake for 40-45 minutes or until a toothpick inserted into the center comes out clean. 
  8. Gently run a knife along the edge to loosen the cake, cover with a large plate or serving platter and carefully invert the cake. Leave the pan on top of the cake for 10 minutes* before removing, slicing and serving. Serve with whipped cream and an additional Mezzetta® Maraschino Cherry on top. 
  9. Enjoy! 

Chef's Note

Leaving the pan on top of the cake after it is inverted ensures that the cake will absorb all of the buttery, sugary goodness of the topping.