Pineapple Upside Down Cupcakes


I’m definitely adding these delicious Pineapple Upside Down Cupcakes to my list of favorite cupcakes! Not that that list really exists other than in my mind, but these are totally there. I love these so much because they are just one of those good old fashioned recipes like your mom or grandma used to make, but they’ve been slightly modernized in cupcake form or “mini pineapple upside down cakes”.

Pineapple Upside Down Cupcakes With Cherry and Whipped Cream

I could eat three of them in one sitting no problem, which is why I’m making them again tomorrow for the second time this week! I’m having family over for a ham and potato dinner (my mom makes the best ham gravy) and I thought these would be the perfect finish for that meal. Pineapple and ham it just goes together, right?

How To Make Pineapple Upside Down Cupcakes




Mini Pineapple Upside Down Cakes on Cooling Rack

These are actually really easy to make, they require a few steps but it goes pretty fast.  It’s worth the extra steps, I promise. Whatever you do though, don’t leave off the maraschino cherries. It’s just wouldn’t be the same without them.

You can usually find the cherries either by the canned fruit at the grocery store or buy the ice cream cones. My kids go crazy for the things (oh, and me too). I have to hide them when I buy them or it’s like the first thing they ask for every day. Smart kids, I mean how could your day go wrong when you start it out with a maraschino cherry? The finer things in life.

Scroll below the recipe to see the steps for making these cupcakes!

Individual Pineapple Upside Down Cakes on Plate

Other Great Cupcake Recipes


Pineapple Upside Down Cupcakes

4.5 from 2 votes

Prep Time: 25 minutes
Cook Time: 25 minutes
Total Time: 50 minutes
Servings: 12
Calories: 324 kcal


  • 1 (20 oz) can pineapple chunks in pineapple juice
  • 1 (8 oz) can pineapple chunks in pineapple juice
  • 1/3 cup (2.7 oz) packed light brown sugar
  • 1/3 cup (2.6 oz) unsalted butter, melted
  • 1 cup (5 oz) all-purpose flour
  • 3/4 cup (5.6 oz) granulated sugar
  • 1/2 tsp baking powder
  • 1/4 tsp salt
  • 1/4 cup (2 oz) unsalted butter, softened
  • 1/2 cup (4 oz) pineapple juice (from pineapple chunk can)
  • 1 large egg
  • 1/2 tsp vanilla extract


  • 3/4 cup heavy cream
  • 2 Tbsp granulated sugar
  • 12 maraschino cherries


  1. Preheat oven to 350 degrees. Spray 12 muffin cups well with non-stick cooking spray.
  2. Drain both cans of the pineapple chunks while reserving 1/2 cup of the juice for batter. Place pineapple over several layers of paper towels to drain well. Melt butter in a microwave safe bowl then stir brown sugar into melted butter. Divide mixture among muffin wells, adding about 2 tsp to each. Arrange pineapple chunks on top of the sugar mixture, about 5 in each (you may not use all of them but I found one 20 oz can wasn't quite enough so I ended up opening 2 cans. The pineapple may be too long to make a flower shape but try to squeeze in 5 of them unless they are large chunks). Set aside.
  3. In the bowl of an electric stand mixer whisk together flour, 3/4 cup sugar, baking powder and salt. Set mixer with a paddle attachment, add butter and pineapple juice then mix until batter is smooth, about 1 - 2 minutes (if using a paddle attachment that doesn't constantly scrape bowl, then occasionally stop mixer and scrape down sides and bottom of bowl throughout mixing process). Mix in egg and vanilla extract until well combined. Divide batter evenly among muffin cups, layering batter over pineapple layer.
  4. Bake in preheated oven until toothpick inserted into into center of cupcake comes out clean, about 23 - 26 minutes. Remove from oven and allow to cool 5 minutes, then run a sharp knife around edges to loosen. Place a wire cooling rack over top of muffin pan and flip to invert onto wire rack. Let cool completely then pipe sweetened whipped cream over cupcakes just before serving and top with a maraschino cherry.
  5. For the sweetened whipped cream:
  6. In a mixing bowl using an electric hand mixer (or in a clean stand mixing bowl set with whisk attachment), whip cream on high speed until soft peaks form. Add sugar then whip until stiff peaks form.
  7. Recipe source: adapted from Bake Create Love
Nutrition Facts
Pineapple Upside Down Cupcakes
Amount Per Serving
Calories 324 Calories from Fat 135
% Daily Value*
Total Fat 15g 23%
Saturated Fat 9g 45%
Cholesterol 57mg 19%
Sodium 64mg 3%
Potassium 187mg 5%
Total Carbohydrates 47g 16%
Dietary Fiber 1g 4%
Sugars 36g
Protein 2g 4%
Vitamin A 11.2%
Vitamin C 12.1%
Calcium 4.9%
Iron 5.1%
* Percent Daily Values are based on a 2000 calorie diet.

Brown Sugar in Cupcake TinAdded Pineapple to Cupcake Pan Cake Batter Added To Pineapple in Cupcake PanBaked Pineapple Upside Down Cupcakes Pineapple Upside Down Cupcakes On Cooling Rack Adding Whipped Cream and Cherry To Pineapple Upside Down Cupcakes


  • Lauren: These are gorgeous! I’m definitely making them for some dinner guests next weekend. How far in advance can I add the whip cream and cherry? I love having a beautiful dessert on display when guests arrive but know that isn’t always possible. Thanks for another great recipe! February 14, 2015 at 5:00pm Reply

    • Jaclyn: You’d be fine to add it an hour maybe even two in advance. I hope you love them :)! February 14, 2015 at 7:49pm Reply

      • Mary: Can I use regular whipping cream January 9, 2016 at 11:17am Reply

  • Anna @ Crunchy Creamy Sweet: Beautiful! I love the full size cake but these cupcakes need to happen soon! February 14, 2015 at 6:32pm Reply

    • Jaclyn: Thanks Anna! February 14, 2015 at 7:48pm Reply

  • Laura (Tutti Dolci): These cupcakes are so, so pretty! Love the whipped cream topping! February 14, 2015 at 11:38pm Reply

  • Leslie: I’ve made these before, they are really good. I think they are really pretty & make a great impression on the plate. February 14, 2015 at 11:57pm Reply

  • Deborah: LOVE!! I did a pineapple upside down cupcake years and years ago that I have been wanting to rephotograph, but they are in a jumbo muffin tin to fit the pineapple. I LOVE that you did chunks like this to make regular cupcakes – just brilliant!! February 15, 2015 at 7:15am Reply

  • Mimi: These look really good! I’ll definitely have to get some pineapple and try these next week. :) February 15, 2015 at 4:26pm Reply

  • Shelby @ Go Eat and Repeat: A close friend of mine makes a similar pineapple cake. While I am not a big fan of the fruit, this definitely makes me want more of it! February 15, 2015 at 5:58pm Reply

  • A Taste Of Madness: I love this idea! So cute :) February 15, 2015 at 8:49pm Reply

  • Katie: What a great idea, they look fabulous. The perfect dessert. Love the glossy cherries on top. So pretty February 16, 2015 at 12:25am Reply

  • Jackie: Hi
    How long do these cupcakes keep with the whipped cream on them. February 17, 2015 at 9:53pm Reply

    • Jaclyn: They should keep a few hours like that as long as they are refrigerated. February 17, 2015 at 11:19pm Reply

  • Beverly in Mississippi: Hi Jaclyn, These are sooooo pretty and I know they are good. My son came home and had one in a napkin. He thought they were great. Now I can make some too! Thanks for sharing. February 20, 2015 at 6:06pm Reply

  • nadia: these cupcakes are amazing and delicious, thank you. March 6, 2015 at 12:18am Reply

  • Maddie: How should we store these when we have not piped whipped cream on them? How long will they last? March 9, 2015 at 10:55am Reply

    • Jaclyn: They could be kept stored in the refrigerator several days in an airtight container. I recommend letting them rest at room temp a bit before serving though then add the whipped cream topping. Hope you love them! March 15, 2015 at 2:49pm Reply

  • Jan Woddail: Would like to try this with peaches. Would make a great peach cobbler! March 20, 2015 at 8:55am Reply

  • Ann: Can these be made ahead and frozen (without the whip cream and cherry?) March 20, 2015 at 8:12pm Reply

    • Jaclyn: I haven’t tried but I imagine that should be fine. April 15, 2015 at 10:26pm Reply

  • Karla: We made these for a dinner party that consisted of all newly pinned recipes. Definitely the best bite of the night! Thank you March 22, 2015 at 12:01am Reply

  • Amanda Dickson: Wow! These look beautiful and scrumptious! I think I may have just found Easter dessert. Thank you!! April 2, 2015 at 1:34pm Reply

  • Leslie Brew: If I’m planning on making these the day before would it be OK to leave them at room temp until the next day, then pipe the whip cream on? I know my cupcakes get a little dried out in the fridge and don’t quite taste the same after being refrigerated. Thanks!! Can’t wait to make these! April 3, 2015 at 10:50pm Reply

    • Jaclyn: I think because of the fruit they are supposed to be refrigerated but mine were fine in the fridge as long as you seal them in an airtight container and let them rest at room temp a bit before serving they should be just fine. April 4, 2015 at 12:54am Reply

  • Mady: Just made these amazing cupcakes! My family loved them. Substituted the cake part for a gluten-free vanilla cake and it worked really well! Thanks for the awesome recipe. June 25, 2015 at 11:40pm Reply

    • Jaclyn: I’m so glad you liked them and that you were able to make them gluten-free! Thanks for your feedback Mady! June 26, 2015 at 2:52pm Reply

    • Melissa: I’d love to see your gluten free cake recipe if you don’t mind sharing. Thanks! July 11, 2015 at 8:56pm Reply

  • Mimi: I made these today using a regular yellow cake mix. They have turned out great, and I have 24 cupcakes for a BBQ with friends. August 5, 2015 at 4:12pm Reply

  • Lynda: Can these muffins be frozen? August 10, 2015 at 8:28am Reply

    • Jaclyn: That should be fine (without the topping on them). I hope you try them and love them! August 12, 2015 at 5:02pm Reply

  • Melanie: I’ve made these twice now! I LOVE them & so does everyone else who’s tried them. The 2nd try I opted for coconut whipped cream (1 c. Whipping cream, 1/2 tsp coconut extract, 2 tbsp. sugar), which was a fun addition! These are so easy and so delicious! Thanks for sharing! August 21, 2015 at 11:26pm Reply

  • stephanie Packer: This is my favorite cake ever, so a cupcake is just fabulous! Last time we made these for a girls night in, we pared them with a pineapple upside-down cake martini! It was wonderful! Thank you for a great recipe! ♡ September 21, 2015 at 4:52am Reply

  • Arlene: Such a great idea! Thanks…will definitely try September 22, 2015 at 5:18am Reply

  • Dana: My daughter has never had pineapple upside down cake before, but these are so gorgeous she chose them as her 7th birthday cake! They’re baked and we’re all anxiously awaiting tomorrow. :) October 2, 2015 at 10:51pm Reply

    • Jaclyn: I hope everyone loves them! Happy Birthday to her! October 4, 2015 at 12:14am Reply

  • donna: can I make these in a mini muffin pan— and how long to bake in oven. I’m having a tea party and need all tea sandwiches and mini deserts. Thank You November 13, 2015 at 8:02am Reply

  • Vicki: My question is the same as Donna, would like to make this recipe in mini muffin tins…is it possible? Thanks! December 14, 2015 at 8:48pm Reply

    • Jaclyn: I haven’t tried so I can’t say for sure but I imagine it would work. I just don’t know what the proportions would be to each. December 14, 2015 at 9:15pm Reply

  • Melanie: I’ve made these 3 times, they are delicious! However, the last 2 times I’ve made them, the butter/sugar mixture bubbles over and causes a smoky, bubbly mess in the oven. It didn’t happen the first time I made them. Am I adding too much? I evenly divide the butter/sugar mixture into my 12 cupcake pan… December 31, 2015 at 4:57pm Reply

  • Manda: My favorite cake ever is the pineapple upside down cake so I cannot wait to try these! Thank you for sharing! Maybe the next recipe suggestion could be a Ham & Potato dinner with Mom’s gravy…? Lol! Thanks, again! January 6, 2016 at 3:29pm Reply

  • erika: Can You substitute regular sugar instead of brown sugar? January 10, 2016 at 3:59pm Reply

  • Lisa Trueper: I have made these before & they are absolutely delicious! Love the portability & cuteness in a cupcake! January 12, 2016 at 10:02am Reply

  • Janice: Thank you for sharing this recipe. I made this for a birthday party and it look and tasted really good. February 20, 2016 at 6:58pm Reply

  • Vicki: I followed this recipe except I substituted rhubarb pieces cut to the same size as the pineapple chunks and it was fabulous! My husband loves it when I use his “pride and joy” spring rhubarb! Oh, and I did peel some of the strings from the rhubarb, easier to cut and eat!! April 8, 2016 at 9:28pm Reply

  • Celeste Estrada: Hello I love these cupcake but I was wondering to make a full cake with this recipe would it be the same amount of ingridents?? :) April 21, 2016 at 12:26am Reply

  • Denise: I have a luncheon for 50 on Saturday, how
    far in advance can I make these? May 2, 2016 at 11:19am Reply

    • Jaclyn: I think they are best the day of but you could make them the day before and store them in the fridge. Then let rest at room temp before serving. May 2, 2016 at 12:15pm Reply

  • Sarah Parker: Just made these for Father’s Day and they were DELICIOUS!!! Cake was light and the recipe was perfect, the cups overflowed a little and formed some nice caramel on the pan, but the nonstick spray made it easy to clean up. Everything turned out amazing, I wouldn’t change a thing! June 18, 2016 at 7:08pm Reply

    • Jaclyn: So glad to hear Sarah! June 21, 2016 at 10:36am Reply

  • Jen: Just made that today and i already want to make more! These are truly amazing!!! The only thing i did differently was to add some vanilla extract to the icing to sweeten it up a little more. My family devoured these and even my husband who rarely eats sweets wanted more. Thank you so much for sharing! June 25, 2016 at 1:36pm Reply

    • Jaclyn: So glad they were enjoyed Jen! July 19, 2016 at 12:38pm Reply

  • theresa: Baking these right now and the brown sugar butter mixture overflowed from a couple of them onto the bottom of my oven. Hope the smoke its creating doesn’t affect the taste of the cupcakes! July 10, 2016 at 3:20pm Reply

    • Jaclyn: Sorry that happened I’ve made these several times and it’s never happened with mine, I wonder if your pan may be a tad smaller or something. Next time I’d put a baking sheet on the rack underneath them though, sorry! July 10, 2016 at 9:48pm Reply

  • Teresa: I made these for the 2nd time today, made a double because everyone loved them so much the first time. Mine overflow a little bit, so I put some foil underneath this time. Still come out great though July 13, 2016 at 4:56pm Reply

  • nidia: hello i have a question. can i make this days before the event? August 21, 2016 at 10:08pm Reply

  • Puding alpukat: These cupcakes are so, so pretty! Love the whipped cream topping September 6, 2016 at 4:51am Reply

  • Abney: How much butter goes into the brown sugar and how much butter goes into the batter? September 6, 2016 at 1:22pm Reply

  • jacque kurz: Made these and they were absolutely delicious. The down side was that my cake part was super moist….almost soggy. Not sure what went wrong…but like I said they tasted great. September 29, 2016 at 9:59am Reply

  • barb: LOOKS YUMMY. November 29, 2016 at 12:54pm Reply

  • sandy: How many. Calories and carbs is. In one pineapple upside. Down cupcakes January 3, 2017 at 7:09pm Reply

  • Akanchha: Can the eggs be replaced for anything else so that the taste and fluffiness is not comprmised? January 16, 2017 at 7:31am Reply

  • Maria: I made this recipe. It is very delicious. We loved it. Will make it again. Yum yum January 22, 2017 at 4:04pm Reply

  • Peggy: Loved this recipe. Great dessert for Easter. By the way, you mentioned that your mom make great ham gravy. How about posting that recipe. Would be very interested. August 9, 2017 at 2:35pm Reply

  • Lucia: Lindos, deve ser deliciósos!!!!! August 15, 2017 at 10:23am Reply

  • Maria: I made this. It was very good. I already made it twice. August 22, 2017 at 6:29pm Reply

    • Jaclyn: So glad to hear it! August 23, 2017 at 11:21am Reply

  • Michel Rivoire: I can’t find where it says how much butter is in the batter and how much is mixed with the brown sugar. September 5, 2017 at 6:21pm Reply

  • Sabrina: Do they taste better after they have been refrigerated? Or are they best at room temperature? September 21, 2017 at 5:24pm Reply

  • Melissa: These were easy and delicious! I did need a bit more whip cream topping, though. I would make 1.5 portions of the recipe. December 5, 2017 at 3:16pm Reply

    • Jaclyn: Glad you liked them, thanks for your feedback Melissa! December 5, 2017 at 4:26pm Reply

  • kathy: can you use the paper liners? My muffin pans are old and a mess. December 28, 2017 at 5:21pm Reply

  • Lola Martinez: These were wonderful! Five stars! March 15, 2018 at 5:27pm Reply

  • A Diaz: Just made these and had to taste before guests arrived… they are fabulous (even without the whipped cream and cherry). I used a gluten free flour substitute and they turned out great. Can’t wait to serve them tonight. Thanks! April 1, 2018 at 2:10pm Reply

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