What makes these Oreo cheesecake cups award winners? You’re going to love this story… It’s about a Mom and a daughter. Yep, me and Kylie.

It’s Elementary, My Dear

It’s no secret that I’ve always loved to bake and spend time in the kitchen.

So, you can imagine my excitement when Kylie was in elementary school and brought home a flyer announcing that a BAKING CONTEST was going to be part of her school’s Holiday Workshop night.

Are you picturing me doing a happy dance? Imagine Snoopy frolicking around on his tippy toes. That was me.

But Kylie? Not so much.

If you met my sweet girl today, you would be impressed by her outgoing nature, her ease with adults, and the kindness you hear when she says hello. She is a confident, smart, kind, and caring young adult. I’m so proud of her.

But as a child, Kylie was quiet and a bit insecure. It wasn’t easy for her to connect with other kids her age. And so the idea of a baking contest? Just the word “contest” made her anxious… so it was not something she was ready to embrace.

Everyone parents differently. My folks taught me that risks are worth taking. And that there is a lot to learn from both success and failure. I wanted that for Kylie and figured a baking contest was a gentle way to give things a shot.

I’m not so sure she was into this idea at first, but I tried my best to make it a fun thing for us to do together.

The Winning Recipe

“What’s your favorite dessert, Kylie?’ I asked.

“CHEESECAKE!” she exclaimed. No problem… except that baking a cheesecake can be a bit testy and I wanted to find a recipe for success.

Related: Creamy and Delicious Baked Cheesecake

So, after rummaging through recipe cards and old cookbooks, I ran across the recipe for these cheesecake cups. The fact that they were an OREO cheesecake cup inspired Kylie even more!

And so we baked together. She did all of the work. The mixing, the pouring, the decorating of the finished cups.

I was her culinary cheerleader, talking her through each step, and reminding her that no matter what happens, how great is it that we have extras for us?

Related: Cookies and Cream Fudge

We placed those Oreo cheesecake cups on a pretty holiday plate and drove them over to the school for the judges to taste.

As we walked back to the car, I looked over at her and told her how proud I was of her and that I thought they were the best cheesecake cups I had ever tasted.

I’ll never forget this next moment. She looked up at me and smiled and said, “me too.”

Cheesecake Cup Champions!

You kind of know what happened next right? We drove back to the school that evening for the holiday bazaar with all kinds of excitement and anticipation.

The event is for the kids to make holiday crafts for their families, but I was totally distracted by wanting to find the baking contest table and the winners.

Related: My All-Time Favorite Desserts

And as we walked up to the table, I spotted our pretty holiday plate. And then I told Kylie to go look at our plate on the table. There it was. 1st place.

Are you crying? Because I am as I’m typing this! I was so happy for Kylie. She had something. All hers. A winner. Well, as you can imagine, she floated for the rest of the night and we couldn’t wait to get home to tell Doug and Trevor.

So, back to these Oreo cheesecake cups. Yep, award-winning. With the taste of success in every bite. Enjoy!

Oreo Cheesecake Cups
Yield: 24 cups

Oreo Cheesecake Cups

Cook Time: 20 minutes
Total Time: 20 minutes

These Oreo Cheesecake Cups are award-winning. Yep, award winning! With the taste of success in every bite. Enjoy!


  • 3 (8 oz) packages regular cream cheese brought to room temperature
  • 3/4 cups sugar
  • 3 eggs
  • 1 tsp vanilla
  • 24 Oreo cookies
  • 3 oz chocolate chips (optional)
  • Additional Oreo cookies, crumbled


  1. Preheat over to 350°. Use paper cupcake liners and line 12 cup muffin tin.
  2. Place each Oreo cookie in a paper liner in a muffin tin.
  3. Beat together the softened cream cheese, sugar, and add the eggs one at a time.Mix until creamy.
  4. Add vanilla and mix through.
  5. Spoon some of the cream cheese mixture over each cookie. Fill cups about 2/3 of the way full.
  6. Bake at 350° for 15-20 minutes or until center is ALMOST set. Don’t over-bake these!
  7. Let cupcakes cool. If desired, melt the chocolate chips and drizzle each cheesecake with chocolate, or use crushed Oreos as a topping.
  8. Refrigerate overnight and then serve when ready

And as you can imagine, the story of her “Golden Spoon” trophy and her baking success is a family favorite. Kylie is in her 20s now and when I recount this story, Kylie has the sweetest smile on her face.

A recipe for success, indeed.

From my family kitchen to yours,

Jill and Kylie

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