Mini Pineapple Upside Down Cheesecakes

Category: Exquisite Sweet Finales

These mini pineapple upside down cheesecakes offer the perfect harmony of creamy cheesecake and caramelized fruit. With a crisp graham cracker crust, tangy cream cheese filling, and a topping of sweet pineapple and maraschino cherries, each bite is bursting with bright tropical flavor and a rich, velvety texture. Baking them in muffin tins ensures individual portions that chill quickly and serve beautifully for gatherings or family treats. The simple process of layering, baking, and chilling yields an eye-catching, crowd-pleasing finale for any meal.

Sandra
By Sandra Sandra
Updated on Wed, 30 Jul 2025 12:03:48 GMT
A dessert with a cherry on top. Pin
A dessert with a cherry on top. | howtogourmet.com

Mini pineapple upside down cheesecakes strike the perfect balance between creamy and bright. Each little cake offers layers of tangy cheesecake, buttery graham cracker crust, and a sweet caramelized pineapple topping crowned with a cherry. These minis are my favorite to bring to spring brunches because they never last more than a few minutes on the dessert table.

I first whipped these up for a family get-together and everyone insisted on taking extras home. Now they are a holiday staple I make for both kids and adults.

Ingredients

  • Crushed graham crackers: This creates a sturdy, buttery base. Make sure the crumbs are fine for the best texture
  • Sugar: Adds sweetness and helps the crust hold together. Look for white granulated sugar that pours easily
  • Melted butter: Binds the crust and gives a rich flavor. Use real butter for best results
  • Cream cheese: Provides the creamy tangy structure. Full-fat block cream cheese works best for the smoothest filling
  • Sugar: Gives the cheesecake its signature sweetness. Use fresh sugar with no clumping
  • Vanilla extract: Rounds out the flavor with warm notes. Pure extract makes a difference if you have it
  • Large eggs: Bind the batter and help the cheesecakes rise. Bring to room temperature for easy blending
  • Crushed pineapple: The star of the topping. Drain well and choose pineapple that smells sweet not fermented
  • Brown sugar: Melts to create a caramel-like topping. Pack it tight so you get rich flavor in every bite
  • Maraschino cherries: Add that iconic pop of color. Look for firm brightly colored cherries

Step-by-Step Instructions

Make the Crust:
Mix crushed graham crackers sugar and melted butter in a bowl until the mixture feels like wet sand. Firmly press it into the bottoms of each muffin cup so the layer is even and compact
Prepare the Cheesecake Filling:
Beat softened cream cheese sugar and vanilla together until completely smooth with no lumps. Add the eggs one by one mixing well between each so the batter stays airy. Gently fold in the drained crushed pineapple last so the filling is well distributed
Assemble the Mini Cheesecakes:
Spoon the cheesecake mixture over each crust dividing evenly. If needed smooth the tops with a small spatula so they bake evenly
Add the Topping:
Sprinkle brown sugar on the surface so each cake will caramelize on top while baking. Place a cherry right in the center of each one
Bake and Cool:
Place the muffin pan in a preheated 325 degree oven. Bake for about 20 to 25 minutes until the cheesecakes look set at the edges and just a little jiggle remains in the center. Let cool completely before trying to remove them for the cleanest results
A plate of desserts with cherries on top. Pin
A plate of desserts with cherries on top. | howtogourmet.com

One year we doubled the recipe for a summer BBQ and had none left by the end of the night. My niece loved helping press the crusts and always requests extra cherries on hers.

Storage Tips

Refrigerate the cheesecakes in an airtight container for up to four days. They also do well if you freeze them tightly wrapped for up to one month. Defrost overnight in the fridge and they honestly taste just as creamy as fresh.

Ingredient Substitutions

You can swap crushed vanilla wafers for graham crackers if preferred. Coconut or pecan pieces mixed into the crust is a tasty twist. Fresh pineapple chunks work as long as you finely chop and drain well. And if you want a lighter version try neufchatel cheese in place of some cream cheese.

Serving Suggestions

These look beautiful on a tiered dessert tray with extra cherries scattered around. It is fun to set out small bowls of whipped cream or a drizzle of caramel for guests to customize their own treats at parties. At home we sometimes add a sprinkle of toasted coconut before serving too.

A slice of pineapple upside down cake. Pin
A slice of pineapple upside down cake. | howtogourmet.com

Cultural and Historical Context

Pineapple upside down cakes have roots in American home baking dating back to when canned pineapple was first popularized in the early 1900s. Turning them into mini cheesecake cups is a modern twist that combines two beloved desserts and makes portioning a breeze.

Recipe FAQs

→ What type of pineapple works best for this dessert?

Both fresh and canned crushed pineapple work well. Make sure to drain thoroughly to avoid excess moisture.

→ How do you prevent the cheesecakes from sticking to the pan?

Use paper liners or lightly grease the muffin tin before adding the crust and filling to ensure easy release.

→ Can these be made ahead of time?

Yes, chill them after baking for several hours or overnight. This helps set the texture and makes serving easier.

→ What is the best way to serve these mini cheesecakes?

Serve chilled, optionally topped with whipped cream and extra cherries for a decorative touch.

→ How do I achieve a smooth cheesecake filling?

Start with softened cream cheese and beat until creamy before adding sugar, eggs, and other ingredients gradually.

Mini Pineapple Upside Down Cheesecakes

Sweet pineapple and creamy cheesecake combine with cherries for a showstopping bite-sized dessert.

Preparation Time
20 min
Cooking Time
25 min
Total Time
45 min
By Sandra: Sandra

Category: Desserts

Skill Level: Intermediate

Cuisine: American

Yield: 12 Servings (12 mini cheesecakes)

Dietary Preferences: Vegetarian

Ingredients

→ Crust

01 240 g crushed graham crackers
02 50 g granulated sugar
03 115 g unsalted butter, melted

→ Cheesecake Filling

04 450 g cream cheese, softened
05 200 g granulated sugar
06 1 teaspoon vanilla extract
07 3 large eggs

→ Topping

08 150 g crushed pineapple, well drained
09 100 g light brown sugar
10 50 g maraschino cherries, halved

Steps

Step 01

Preheat oven to 160°C. Lightly grease a 12-cup muffin tin or line with paper cases.

Step 02

In a bowl, combine crushed graham crackers with granulated sugar. Pour in melted butter and stir until the mixture resembles wet sand. Evenly press the mixture into the base of each muffin cup and compact with the back of a spoon.

Step 03

In a separate mixing bowl, beat softened cream cheese with granulated sugar and vanilla extract until creamy and smooth. Add eggs one at a time, beating after each addition until fully incorporated.

Step 04

Fold the drained crushed pineapple gently into the cheesecake batter.

Step 05

Spoon the cheesecake mixture over the prepared crusts in the muffin tin, filling each nearly to the top.

Step 06

Sprinkle a layer of light brown sugar over each cheesecake and place half a maraschino cherry in the centre.

Step 07

Bake in the preheated oven for 20–25 minutes, or until the centres are set and the edges are lightly golden.

Step 08

Allow cheesecakes to cool completely in the tin before removing. For best results, chill in the refrigerator prior to serving.

Additional Notes

  1. Use either fresh or thoroughly drained canned pineapple for best results.
  2. Chilling the cheesecakes improves their texture and makes removal from the tin easier.
  3. Serve with a dollop of whipped cream for added richness, if desired.

Required Equipment

  • 12-cup muffin tin
  • Mixing bowls
  • Electric mixer
  • Rubber spatula
  • Measuring cups and spoons

Allergen Information

Always review every ingredient for potential allergens and consult a health professional if you’re unsure.
  • Contains dairy (cream cheese, butter), eggs, and wheat (graham crackers).

Nutritional Information (per serving)

The provided details are for informational purposes and should not replace professional health advice.
  • Calories: 250
  • Fats: 12 g
  • Carbohydrates: 30 g
  • Proteins: 4 g