Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes

I love pineapple. I love cupcakes. So, why not put these two together and create some delicious pineapple upside down cupcakes? Yes, please!

These are super easy and ready in just 45 minutes and you’ll make enough to eat them all week long! Enjoy!

Pineapple Upside Down Cupcakes

Yields: 24 cupcakes


  • ½ cup butter, melted
  • 1 ½ cups brown sugar
  • 24 maraschino cherries
  • 2 (20 ounce) cans crushed pineapple
  • 1 box of yellow cake mix
  • 3 eggs
  • 1 1/3 cups pineapple juice
  • 1/3 cup vegetable oil

Pineapple Upside Down Cupcakes


  1. Move an oven rack into the middle of the oven. Preheat oven to 350 degrees F.
  2. Grease 24 muffin cups.
  3. Line a work surface with waxed paper
  4. Spoon 1 teaspoon melted butter into the bottom of each muffin cup.
  5. Spoon 1 tablespoon brown sugar in each muffin cup.
  6. Press a maraschino cherry into the center of the brown sugar in each muffin cup.
  7. Spoon a heaping tablespoon of crushed pineapple over the cherry and compact it with the back of a spoon into an even layer.Pineapple Upside Down Cupcakes
  8. Mix yellow cake mix, eggs, pineapple juice and vegetable oil in a large bowl with an electric mixer on low speed until moistened, about 30 seconds. Turn mixer speed to medium and mix for 2 minutes.
  9. Pour cake batter into the muffin cup, filling them to the top; do not overfill.
  10. Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.
  11. Allow cupcakes to cool at least 5 minutes before inverting muffin cups onto the wax paper to release. Serve with pineapple and cherry sides up.

Pineapple Upside Down Cupcakes

What’s your favorite type of cupcakes? Comment below and share with us!

Melanie Kampman

Melanie Kampman is a web designer, developer and owner of Giveaway Bandit and Farm News for Kids. She lives in Northwest Missouri on a large family farm with her husband and eight year old son, the Giveaway Bandit. They raise cattle with a variety of pets including horses, chickens, ducks, and a slew of cats. By Melanie Kampman If you are interested in writing a sponsored post on Giveaway Bandit please email me at melanie (at) giveawaybandit (dot) com.

  1. yum this looks so good I love upside down cake my husband loves it to i will try to make this for him denise smith

  2. Yummy! I’m gonna have to make these for my husband. He has been wanting a pineapple upside down cake for a few weeks. He will love the cupcakes. Thanks for the recipe!

  3. These look so amazingly good. I think I will make them for a surprise for my family. I know they will just love them.

  4. oh my these look awesome i love upside down cake but never tried them cupcake style i am sure my kids would have a blast making these

  5. These cupcakes looks so yummy and can’t wait to make. I love pineapple anyway.

  6. My husbands favorite cake is a pineapple upside down cake, he is going to love these! Not to mention the kids as well.

  7. These upside down mini cakes looks so delicious! Looks very easy! Will try this recipe out!

  8. These look absolutely delicious and appear easy to make. Thank you for sharing.

  9. I have not has pineapple upsidedown cake in years..These are so cute and look scrumptious 🙂

  10. this recipe sounds amazing. hubby loves pineapple so this is my next to do baking list thanks for sharing the recipe 😉

  11. These look amazing! I always thought pineapple upside cake was really difficult- but this definitely looks like something I can do! That carmelized crushed pineapple top is just soooooo good!!! Thanks!

  12. I really like this recipe! I think these would be great for a family gathering or pot luck dinner. 🙂

  13. What a great idea! making these into cupcakes really transforms this homey dessert, and boy, does it look good! I’d like to try thi!

  14. I’d make mine without the maraschino cherry. Don’t need that red dye.
    slehan at juno dot com

  15. I have to agree there is nothing like pineapple upside cake, but I never thought about cupcakes.I am going to have to make these this week

  16. These look so yummy and delicious. I saved this to make for my family. Love the individual sized cakes.

  17. Love pineapple upside down cake so would really like these. Recipe looks easy to make and know family will love them. Thanks for sharing.

  18. These look so good. I really like the cupcake idea because then there is some portion control . Goodness knows then I would know when to stop ha! (maybe)

    ellen beck

  19. My neighbor baked some of these and shared with us a couple of weeks ago! They were so yummy! The recipe seems fairly simple, I think I could handle it 🙂

    This is something I REALLY have to try. Soon. Looks so good!
    Digicats {at} Sbcglobal {dot} Net

  21. What a yummy idea, never tried this but it sure does sound delicious and love that they are bite sizes.

  22. I always loved this dessert growing up as a kid. It is so cool to finally be able to make it at home, and, in cupcake form! The best part is always the maraschino cherry (or three or four).

  23. This has always been one of my favorite desserts. This is such a great idea to make the indivual servings.

  24. Pineapple upside down cake is one of my familys favorites. This easy cupcake will make me bake it more often since it is so easy!

  25. Yum, love pineapple upside down cake but the cupcakes look even better. I know I couldn’t eat jut one!

  26. My mother made the best pineapple upside down cake. These cupcakes sound like they would be just as good.

  27. Red velvet cupcakes with buttercream frosting are well-received in my house and so are yellow with chocolate frosting. These Pineapple Upside Down cupcakes would be devoured by my husband!

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