Pineapple Upside Down Cake

It’s been a long time since I’ve had one of these cakes so when my husband mentioned how his mom used to make these, I knew I had to make one for him.  These are SOOOOO much easier to make than I thought they were.  Let’s get started. 


  • 12 slices of pineapple (drained)
  • 12 Maraschino Cherries
  • 1 c. Brown sugar
  • 1 stick of butter
  • 2 c. flour
  • 1Tbs baking powder
  • 1 1/4 c sugar
  • 1 tsp. salt
  • 2 eggs
  • 3/4 c. Milk
  • 1 tsp. Vanilla

  You can delete the last 7 ingredients and just use a yellow cake mix from the box:)  I prefer from scratch though.


Heat oven to 350°F. In 8 x 13 pan, melt butter in oven (or just use the microwave). Sprinkle brown sugar evenly over melted butter. Arrange pineapple slices over brown sugar. Place cherry in center of each pineapple slice.

Beat remaining ingredients with electric mixer on low speed 30 seconds, scraping bowl constantly. Beat on high speed 3 minutes, scraping bowl occasionally. Pour batter over pineapple and cherries.

Bake 50 to 55 minutes or until toothpick inserted in center comes out clean. Immediately place heatproof serving plate upside down over pan and then turn plate and pan over. Leave pan over cake a few minutes so brown sugar mixture can drizzle over cake; remove pan. Serve warm. Store cake loosely covered.






Join The Discussion




  1. 1

    Megan says

    I voted for you! Best food blog.
    5 more entries for the stand-up mixer. ya-hoo

    Megan’s last blog post..Spanish Beef Dips with Carmelized Manchego Onions

  2. 2

    ciara says

    ohmygoodness…this looks so good and so fattening. why, oh, why, do i need to be on a diet right now? lol maybe i could make this and have one little piece. one little piece wouldn’t hurt, now would it? :)

    i voted for your blog, too, i just need to make my post.

    ciara’s last blog post..Linky Love

  3. 3

    lovely says

    hi there…you mean he stick of butter will no longer be included in the batter? it’s placed directly on the pan then topped with sugar and the pineapple? thanks

  4. 4

    Did you happen to leave out an ingredient? I just made this and the batter is VERY sticky and tastes like flour and water ;) Is it missing some sugar? My 5 year old son (birthday today) saw me looking at this post and said THAT is what I want for dessert (he loves pineapples) so we made it. But now we have to make it again using a boxed cake mix. ;) Let me know!

    Heather Neff’s last blog post..Tobias Gregory… age 5

  5. 5

    Annie says

    Yummy! My mom used to make these frequently when I was younger, and now I’m craving one!

    Annie’s last blog post..Childhood Dreams; Shattered

  6. 6

    And yup, my google reader left out the sugar. BUT the cake mix was a hit and they loved it. And Toby was none the wiser. He just wasn’t around when I dumped the other cake and whipped up the new one. He thought he made it. Tee hee. Gotta love tricky moms.

    Heather Neff’s last blog post..What were you doing at 4:00am this morning?

  7. 7

    Linda SS says

    You got my vote on Best Blog – who can resist this scrumptious looking cake:)

  8. 8

    Alright, I’m looking at your recipes and my husband spotted this. He loves this kind of cake and when he saw your pictures he wanted to marry you! LOL! Seriously, now I have to go and buy this stuff and make it. His mouth is watering. I won’t be making this one a healthy recipe. Maybe organic pinapple?

  9. 9

    Barbara Cafarelli says

    Thanks for the recipe.. I have only made it with cake mixes but like to try things from scratch when I can.. This is a favorite of my fiance so its nice to have a good recipe onhand.

  10. 10

    Don’t forget the pecans! Lay pecan halves out in the empty spaces around the pineapple rings – yum! Also, if you have a cast iron skillet, make the whole thing in that and it’s even better! Also, with the drained juice from the pineapple you could either replace some of the water in the recipe with the juice OR when the cake comes out you can poke a few toothpick holes in the bottom (before flipping) and pour some of the juice into the cake for extra moistness.

    RobynLynn Ws last blog post..Google Love

  11. 11

    kg says

    Thank you for this recipe! I kept finding recipes that called for yellow cake mix, so I was glad to find this one. We had been given a fresh pineapple that I knew we wouldn’t consume before it went bad, so I took what chunks we had left and made this cake. And of course I had no yellow cake mix in my pantry, so I wanted a from-scratch recipe. Because we didn’t have much pineapple leftover, I halved the recipe and also substituted a little graham flour for part of the white flour and cut back on the sugar ever-so-slightly. YUM!

    • 12

      Jennifer Hall says

      What kind of cake pan did you use? I have glass pans and coated pan or did you use a cast iron pan? I want to make this cake I just want to find out what type of pan to use I am a beginner baker. Thank you

  12. 14

    tiffany wood says

    made this tonight but it was extra dry… im not sure why… im going to try it with yellow cake mix next time! thank you for the recipe! :O)

  13. 15

    Michelle Daugherty says

    My husband absolutely loves this cake! Your recipe rocks :-) I have made this cake 3 times using your recipe and each time I make it everyone tells me how awesome it is. I read where someone said it was dry–mine always turns out super moist so I was wondering if they left it in the pan instead of turning it over and letting the topping soak in? Thanks for the great recipe, Michelle

  14. 16

    Amanda Zaayer says

    I just made this and while the flavor is very good, the cake is more like pineapple upside down bread. The batter was very thick, the cake very dry. I’m thinking it could use some oil?