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.

  • denise226

    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

  • Lisa Coomer Queen

    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!

  • I like that you did these in a muffin tin. They turned out so good.

  • disappointed

    Omg those are amazing looking im making them tonight lol

  • debbiewelchert

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

  • Shirleyf1972

    Have had the cake but never the cupcake. Need to give it a try.

  • Ricardo

    looks nice, ñam ñam!

  • Erica Weaver

    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

  • I can’t wait to try this recipe! My son makes red velvet cupcakes that I love

  • Linda Flakes

    My Favorite is strawberry cupcakes.

  • Gail Lindsey

    The mini pineapple cakes look so good! Thank you for the recipe Bandit Lifestyle!

  • Carolyn Cheek- Massey

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

  • Sheila Ritter

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

  • Corina Hernandez

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

  • Marcos Batac

    Yummy Like it!

  • Kimberly Flickinger

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

    • sara

      This dessert looks yummy and easy to make

  • kathleenkelly

    Oh, I have to try these! Thanks for sharing!

  • Edward Tavares

    Those look amazing!

  • Shilpa Shetty

    I’m feeling hungry again,.. 🙂 Yummy

  • kathy pease

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

  • Rachel Beltz

    I hate the hassle of large cakes- so these are perfect! Individual little glories!

  • Debbie Snell

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

  • Katy

    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!

  • Betsy R Barnes

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

  • alterlisa

    just pinned this on both my cupcake and easy dessert boards

  • Rosie

    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!

  • tiffany dayton

    We love pineapple upside down cake. I know we will like these.

  • Pops

    They look lovely must try them

  • Karen D

    I never used to like pineapple upside down cake but do now. These look incredible!

  • slehan

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

  • These sound so easy and look so delicious.

  • Nancy Burgess

    These would be my favorite cupcake I love pineapple upside down cake.

  • gmoney222

    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

  • anne marie

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

  • Leslie Crosbie

    These actually sound pretty easy to make, I am going to attempt making this recipe!

  • These cupcakes sound scrumptious! I’ve made a full-size cake similar to this one, but never thought about mini ones! Too cute.

  • Carolyn Cheek- Massey

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

  • Joy Allen

    OMG, these look so good, it’s 9:30am. and i wanna make them now!

  • Jeanna Schirm Massman

    This looks so delicious! I love recipes that are not too complicated.

  • tannawings

    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

  • John Smith


  • Sue M.

    These look really scrumptious! I’ll definitely try out this recipe, thanks a lot for posting!

  • gmoney222

    I made these and they were WONDERFUL………….. gone within 15 minutes

  • geriheartnsoulcooking

    Yummy and so easy, two of my favorite in a recipe

  • clojo9372

    My mother loves Pineapple based desserts, so I know she will enjoy this recipe! 🙂

  • amanda roach

    i love the these are a must try.

  • Laurie P

    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 🙂

  • Michael

    Ill have to try this sometime, looks relatively easy to make!

  • denise low

    Thank you for sharing. I never thought of doing it this way. Great idea.

  • Richard Hicks

    Have not seen this in a cupcake. Something I want to try!

  • kathleenkelly

    I bought all of the ingredients for this but have not made it yet! Probably this week!

  • cezovski

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

  • Omg I love the cake but never thought about this. Can’t wait to try them.

  • Ilya Shcherbatov

    Look tasty, like pineapple

  • Dotty J Boucher

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

  • amycrocker76

    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).

  • Darla Peduzzi

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

  • zenamichele

    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!

  • decsn

    any recipe with Pineapple is superb! thank you for sharing this is yummy!

  • slr11

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

  • Gord

    I love pineapple upside down cake. My gf is going to make these for me.

  • Deborah Clarke

    Looks yum.

  • Jodi Hoppe Wresh

    I love it & definitely have to try this. Will pass in to my mom and sisters as well.

  • inkchick

    Great twist on the classic.

  • Gord

    We tried these and they are delicious! Give em a try!

  • wins4me

    I would love to make these

  • Natalie

    I love that these cakes come in individual servings!

  • Orna Soref

    like it

  • grannyhoff

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

  • 1alwaysnyc1

    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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