These Oatmeal Raisin Cookie Cups are the perfect bite-sized treats. They’re made with soft oatmeal cookie cups filled with raisin pie filling and a simple cream cheese frosting.

I’ll be honest. I never crave raisins on their own. But for some reason, I absolutely love them in other recipes. These Oatmeal Raisin Cookie Cups are one of my favorite raisin recipes (a close second is my broccoli salad!)

These cookies are soft and sweet, and nestled inside is a layer of raisin pie filling and a swirl of cinnamon cream cheese filling. This recipe is phenomenal, so fun, and so simple to make! 

Why You’ll Love Oatmeal Raisin Cookie Cups

• Quick and easy. These cookies are simple and easy if they’re made from scratch and even simpler and easier if you use store-bought cookie mix and pie filling. You can’t go wrong!
• Something different. They’re the perfect way to satisfy that oatmeal raisin cookie craving, but in a unique and fun way.
• Delicious! Turns out, cream cheese and oatmeal raisin are a match made in heaven!

Ingredients

• Oatmeal Cookie Mix – you can use a store-bought cookie mix or make your own oatmeal cookie dough.
• Cream Cheese – be sure to bring the cream cheese to room temperature so it incorporates easily with the other ingredients.
• Powdered Sugar – sweetens the cream cheese and gives it that thick, frosting-like texture.
• Spices – we’re giving the cream cheese frosting a hint of sweet spice with cinnamon and nutmeg.
• Raisin Pie Filling – you can make a homemade batch or use a canned, store-bought version.

How to Make Oatmeal Raisin Cookie Cups

These oatmeal cookie cups take just 15 minutes to prep! Here’s a quick summary of the recipe: 

• Step One: Prepare the cookie dough as instructed. You can use a store-bought package or make your own.
• Step Two: Press the cookie dough into a greased muffin tin and bake for 7 minutes. Remove the tray from the oven, then use a small spoon to deflate the centers of the cup to maintain that cup shape.
• Step Three: Bake for an additional 5 minutes, then remove and deflate again. Bake one more time until the cookies start to turn golden-brown. Remove and cool completely.
• Step Four: In a bowl, mix together whip cream cheese, icing sugar, cinnamon, and nutmeg.
• Step Five: Add 1 teaspoon of raisin pie filling to the bottom of each cooled cookie cup, then use a piping bag to pipe the cream cheese mixture into each cookie cup as well.

Equipment Needed

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• Muffin Pan
• Hand Mixer
• Icing Tips

Recipe Tips and Tricks

• Keep deflating the cookie cups. I know. It’s a little bit hands-on, but it’s necessary for the cookies to maintain that cup shape.
• Don’t over-bake. Take the cookie cups out of the oven as soon as they are starting to turn golden-brown. We want a soft texture, not a crunchy one.
• Let the cookies cool completely. If you add the frosting while the cookies are still hot, it will just melt and make the cookies soggy.

Variations and Substitutions

• Use another cookie dough. In theory, you can use any cookie dough you like! Just make sure you follow the baking instructions specific to that recipe. Not all cookies cook the same.
• Add other mix-ins. Feel free to add other mix-ins to the cookie dough. You could do chocolate chips, chopped walnuts or pecans, or another dried fruit such as craisins or chopped dried cherries.
• Try a different frosting. This recipe works great with any frosting recipe you like!
• If you can’t find raisin filling, you can make your own or opt for a drizzle of caramel or hot fudge sauce instead. You can also just skip the filling entirely and use just the cream cheese frosting.

Storage Instructions

The fully assembled cookie cups should be stored in the refrigerator because of the cream cheese frosting. They will last for 5-7 days. 

You can also store the actual cookie cups before adding the fillings on the counter for up to 5 week or in the fridge for up to a week.

Can I freeze oatmeal raisin cookie cups?

You can, but you should do so without the fillings. To freeze the cookie cups, bake and cool the actually cookie part as instructed, then store them in the freezer for up to 3 months.

When you’re ready to serve them, let them thaw on the counter, then add the fillings and serve!

More Cookie Cup Recipes to Try

• Peanut Butter Cookie Cups
• Caramel Cookie Cups
• Reese’s Peanut Butter Cookie Cups
• Birthday Cookie Cups
• Gooey Cheesecake Cookie Cups

Craving more oatmeal recipes? Try my Oatmeal Cake and Oatmeal Pie! You might also like these Sour Cream Raisin Bars.

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