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5 Surprising Twists on Classic Pineapple Upside-Down Cake

Your favorite vintage dessert just got a modern makeover.

When it comes to classic desserts, we can’t get enough pineapple upside-down cake. There’s something about that soft layer of sponge and gooey, pineapple-y glaze that transports us to holiday heaven. This time-tested treat has been around for over 100 years, so everyone—young and old—will be lining up for a slice.

To celebrate everyone’s favorite cake, we came up with a few fun twists on the treasured recipe. Each one is just as impressive as the original and is ready to make its debut at your holiday celebration. All you have to do is choose the recipe that best fits your needs, pick up a can of DOLE® Pineapple and get ready to make a new holiday memory!

Pineapple Upside-Down Dump Cake

Pineapple Upside-Down Dump Cake

The holidays can be hectic, which is why we like to take a shortcut whenever possible. This delicious dump cake combines pantry staples—like DOLE® Crushed Pineapple and cake mix—in your slow cooker. It’s the perfect treat for a family movie night, holiday open house or any casual gathering.

Prep: 10 min. Cook: 2 hours + standing


  • 3/4 cup butter, divided
  • 2/3 cup packed brown sugar
  • 1 jar (6 ounces) maraschino cherries, drained
  • 1/2 cup chopped pecans, toasted
  • 1 can (20 ounces) DOLE® Pineapple Tidbits or Crushed Pineapple (in juice), undrained
  • 1 package yellow cake mix (regular size)
  • Vanilla ice cream, optional


1. In a microwave, melt 1/2 cup butter; stir in brown sugar. Spread evenly onto bottom of a greased 5-qt. slow cooker. Sprinkle with cherries and pecans; top with DOLE Pineapple. Sprinkle evenly with dry cake mix. Melt remaining butter; drizzle over top.

2. Cook, covered, on high until fruit mixture is bubbly, about 2 hours. (To avoid scorching, rotate slow cooker insert one-half turn midway through cooking, lifting carefully with oven mitts.)

3. Turn off slow cooker; let stand, uncovered, 30 minutes before serving. If desired, serve with ice cream. Yield: 10 servings.

Pineapple Upside-Down Cupcakes

Pineapple Upside-Down Cupcakes

Instead of worrying about cutting cake into perfectly even slices, whip up a batch of pineapple upside-down cupcakes instead. All of your holiday guests will get their own treat. Plus, you can cut down on pre-party stress by making these beauties the day before. Just top with a dollop of whipped cream right before serving.

Prep: 30 min. Bake: 30 min. + cooling


  • 6 tablespoons butter, cubed
  • 1 cup packed light brown sugar
  • 2 tablespoons light corn syrup
  • 12 DOLE® Pineapple Slices (1 20-ounce can plus half 8-ounce can)
  • 12 maraschino cherries, well drained
  • 3 large eggs, room temperature
  • 2 cups sugar
  • 1 cup canola oil
  • 1 cup sour cream
  • 2 teaspoons vanilla extract
  • 2-1/2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon salt
  • Whipped topping, optional


1. Line the bottom of 12 greased jumbo muffin cups with waxed paper; grease the paper and set aside.

2. In a small saucepan, melt butter over low heat; stir in brown sugar and corn syrup. Cook and stir over medium heat until sugar is dissolved. Remove from the heat. Spoon 1 tablespoonful into each muffin cup; top each with a DOLE Pineapple Slice and a cherry.

3. In a large bowl, beat eggs and sugar until thickened and lemon-colored. Beat in the oil, sour cream and vanilla until smooth. Combine the flour, baking powder, baking soda and salt. Add to egg mixture and mix well.

4. Fill muffin cups two-thirds full. Bake at 350° for 28-32 minutes or until a toothpick inserted in the center comes out clean.

5. Cool for 5 minutes before inverting onto wire racks to cool completely. Garnish with whipped topping if desired. Yield: 1 dozen jumbo cupcakes.

Mini Pineapple Upside-Down Cake

Pineapple Upside-Down Cupcakes

You deserve a holiday treat, too. And this mini upside-down cake is the perfect size to split with a loved one (or save for later). It’s ready to eat in under an hour, and all that’s missing is a scoop of vanilla ice cream. Now, go grab a fork!

Prep: 15 min. Bake: 30 min.


  • 1 can (8 ounces) DOLE® Pineapple Slices
  • 1/4 cup packed brown sugar
  • 3 tablespoons butter, melted, divided
  • 4 maraschino cherries
  • 4 pecan halves
  • 3/4 cup all-purpose flour
  • 1/3 cup sugar
  • 1 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1/8 teaspoon ground allspice
  • 1 egg, lightly beaten
  • 1/4 cup 2% milk


1. Drain DOLE Pineapple Slices, reserving 1 tablespoon juice. Set pineapple aside. In a small bowl, combine brown sugar and 2 tablespoons butter; stir until sugar is dissolved.

2. Pour into an ungreased 6-in. round baking pan. Arrange pineapple slices in a single layer in pan; place cherries and pecans in center of pineapple slices.

3. In a small bowl, combine the flour, sugar, baking powder, salt and allspice. Beat in the egg, milk, reserved pineapple juice and remaining butter just until combined. Spoon over pineapple.

4. Bake at 350° for 30-35 minutes or until cake springs back when lightly touched. Cool for 5 minutes before inverting onto a serving plate. Serve warm. Yield: 4 servings.

Pineapple Upside-Down Cheesecake

dole pineapple upside cake

For a show-stopper, look no further. This decadent mashup combines two of your favorite treats into one dazzling display. The gooey, glazed fruit pairs well with the creamy cheese layer, while a sprinkling of cinnamon graham cracker crumbs take this treat over the edge. Trust us when we say that this cheesecake will impress everyone at the table.

Prep: 25 min. Bake: 35 min. + chilling


  • 3/4 cup packed brown sugar
  • 1 can (8 ounces) DOLE® Pineapple Slices
  • 4 maraschino cherries

For the filling:

  • 1 package (8 ounces) cream cheese, softened
  • 1/2 cup confectioners’ sugar
  • 2 teaspoons all-purpose flour
  • 1 teaspoon vanilla extract
  • 1 large egg, lightly beaten
  • 1/4 cup DOLE Crushed Pineapple, well drained

For the crust:

  • 1 tablespoon butter
  • 1/3 cup graham cracker crumbs
  • 1/4 teaspoon ground cinnamon


1. Preheat oven to 325°. Sprinkle brown sugar into an 8-in. ovenproof skillet. Arrange pineapple in a single layer over brown sugar; place a cherry in the center of each DOLE Pineapple Slice.

2. For filling, in a large bowl, beat cream cheese and confectioners’ sugar until smooth. Beat in flour and vanilla. Add egg; beat on low speed just until blended. Fold in DOLE Crushed Pineapple. Spoon over fruit.

3. Bake 35-40 minutes or until center is almost set. Cool on a wire rack 10 minutes. Loosen sides from pan with a knife. Cool 1 hour longer. Refrigerate overnight, covering when completely cooled.

4. For crust, in a small skillet, melt butter over medium-low heat. Add cracker crumbs and cinnamon; cook and stir 4-6 minutes or until toasted. Cool. Just before serving, top cheesecake with toasted crumbs, pressing to adhere. Invert cheesecake onto a serving plate. Yield: 4 servings.

Pineapple Upside-Down Muffins

Pineapple Upside-Down Muffins

Planning a holiday brunch? These morning muffins will brighten everyone’s day. Plus, this recipe yields either 3 dozen mini muffins or 10 regular-size treats, so it’s perfect for gatherings big and small. No one will be able to resist the cute cherry on top!

Prep: 25 min. Bake: 10 min.


  • 1 can (8 ounces) DOLE® Crushed Pineapple
  • 1-1/2 cups all-purpose flour
  • 3/4 cup sugar
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 2 large eggs, room temperature
  • 1/2 cup vanilla yogurt
  • 1/4 cup canola oil
  • 5 teaspoons brown sugar
  • 18 to 20 maraschino cherries, halved


1. Preheat oven to 400°. Drain DOLE Crushed Pineapple, reserving 1 tablespoon juice. Set pineapple aside.

2. In a large bowl, whisk flour, sugar, baking powder and salt. In another bowl, whisk eggs, yogurt, oil and reserved pineapple juice. Add to flour mixture; stir just until moistened. Fold in reserved pineapple juice.

3. Fill greased mini-muffin cups two-thirds full. Sprinkle tops with brown sugar; top with halved cherries.

4. Bake 9-12 minutes or until a toothpick inserted in center comes out clean. Cool 5 minutes before removing from pans to wire racks. Serve warm. Yield: About 3 dozen mini muffins or 10 regular muffins.

Editor’s Note: If you’re using regular-size muffin cups, reduce maraschino cherries to 5 and bake for 12-16 minutes.

For more great holiday recipe ideas, visit