Cake

Pineapple Upside-Down Cake with Maraschino Cherries

Pineapple rings and maraschino cherries caramelised in brown sugar and butter on top of a golden round cake.

60 min · 8 slices · Round inverted cake

A round upside-down cake crowned with caramelised pineapple rings and a maraschino cherry in each ring, over a golden crumb

About Darleen

on Recipesdarleen

Darleen is a mom who turned her slow cooker into a lifesaver, sharing cozy, easy-to-make recipes that bring comfort to busy days.

268 recipes by Darleen Vance

Published November 29, 2025

How Recipesdarleen publishes recipes

Butter is melted in the cake pan, brown sugar is scattered over it, and seven pineapple rings go on top with a cherry in the middle of each.

The batter uses pineapple juice and milk as its liquid, and after baking the cake rests 10 minutes before it is turned out.

Built Upside Down

What goes in the pan first ends up on top.

  1. Batter

    Spread over the fruit, becoming the base once turned out.

  2. Fruit

    Seven pineapple rings, each with a cherry.

  3. Brown sugar

    Half a cup, scattered evenly.

  4. Butter

    Four tablespoons, melted in the pan.

How to Make It

  1. Caramel base

    Heat oven to 350°F. Melt 4 tablespoons unsalted butter in a 9-inch round cake pan and sprinkle packed light brown sugar evenly over it.

  2. Fruit arranged

    Arrange canned pineapple rings over the sugar and place a maraschino cherry in each ring.

  3. Dry mix

    Whisk all-purpose flour, baking powder, and fine salt.

  4. Creamed

    Beat softened unsalted butter with granulated sugar. Beat in large eggs and vanilla extract.

  5. Batter over fruit

    Add the dry ingredients alternately with pineapple juice and whole milk. Spread the batter over the fruit.

  6. Baked and inverted

    Bake 38 to 42 minutes, until a tester comes out clean. Cool 10 minutes, then invert onto a serving plate.

Why This Recipe Works

  • Melting the butter in the pan starts the caramel where it will end up.
  • Pineapple juice in the batter carries the fruit flavour into the crumb.
  • Alternating dry ingredients and liquid keeps the batter smooth.
  • A 10-minute rest lets the caramel settle before inverting.

Ingredient Notes

Pineapple rings
Seven canned rings, drained.
Maraschino cherries
Seven, one in each ring.
Pineapple juice
Half a cup, used in the batter.

Success Tips

  • Pat the pineapple rings dry so the caramel does not turn watery.
  • Spread the batter gently so the fruit stays in place.
  • Invert with oven mitts, holding plate and pan together.

Serving Ideas

Serve warm or at room temperature, cut into eight wedges.

Storage and Reheating

Refrigerate

Cover and refrigerate up to 4 days.

Frequently Asked Questions

When should I turn it out?

After 10 minutes; the caramel is still hot, so handle it carefully.

How do I know it is baked?

A tester in the center comes out clean.

Recipesdarleen

Pineapple Upside-Down Cake with Maraschino Cherries

Pineapple rings and maraschino cherries caramelised in brown sugar and butter on top of a golden round cake.

Prep
20 min
Cook
40 min
Total
60 min
Yield
8 slices

Round inverted cake

Equipment9-inch round cake pan · Electric mixer · Serving plate

Ingredients

Instructions

  1. Heat oven to 350°F. Melt 4 tablespoons unsalted butter in a 9-inch round cake pan and sprinkle packed light brown sugar evenly over it.
  2. Arrange canned pineapple rings over the sugar and place a maraschino cherry in each ring.
  3. Whisk all-purpose flour, baking powder, and fine salt.
  4. Beat softened unsalted butter with granulated sugar. Beat in large eggs and vanilla extract.
  5. Add the dry ingredients alternately with pineapple juice and whole milk. Spread the batter over the fruit.
  6. Bake 38 to 42 minutes, until a tester comes out clean. Cool 10 minutes, then invert onto a serving plate.