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Apple Crisp Cookie Cups

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These Apple Crisp Cookie Cups combine classic oatmeal cookies with homemade apple pie filling for the perfect comfort food.

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I am eternally grateful to friends and family members who help me come up with recipe ideas. Sometimes I have a list of things I want to bake, but inevitably that runs out and then, in a panic, I ask people for suggestions.

The idea for these Apple Crisp Cookie Cups came from my friend Sharai who loved my Caramel Cookie Cups so much that she wanted to come up with alternatives that I could make and she could eat. Who am I to say no to that?

These Apple Crisp Cookie Cups combine classic oatmeal cookies with homemade apple pie filling for the perfect comfort food. | livforcake.com

I know apples and apple pie are technically more of a fall dessert, but really there’s no bad time for apple pie anything. These apple crisp cookie cups are really simple to make. I used my favourite Oatmeal Cookie recipe, minus the chocolate chips as the “crust”.

I used a large cookie scoop to portion the dough into grease muffin tins, baked them up, and then pressed a small container into the center of each one once they were out of the oven. This needs to be done while the cookies are still HOT, so be careful not to burn yourself.

These Apple Crisp Cookie Cups combine classic oatmeal cookies with homemade apple pie filling for the perfect comfort food. | livforcake.com

The apple pie filling is really easy too — chop up some apples, throw them into a pot with some ingredients and cook until tender. You’ll want to cool the cookies and the apple pie filling completely before assembly. I made both the day before, but you could make them all in the same day as long as everything cools.

These Apple Crisp Cookie Cups combine classic oatmeal cookies with homemade apple pie filling for the perfect comfort food. | livforcake.com

I topped some of these with a simple sugar glaze, but you could use whipped cream or even ice cream if you prefer. Or just eat them straight up like I did.

These Apple Crisp Cookie Cups combine classic oatmeal cookies with homemade apple pie filling for the perfect comfort food. | livforcake.com

I recommend microwaving the cookie cups for a few seconds so you get that fresh baked apple crisp taste and texture. The kids are sure to love these. Bite sized and delicious!

You will love these Apple Crisp Cookie Cups. They are delicious any time of year!

Be sure to check out my other cookie cup recipes!

Notes & tips for these Apple Crisp Cookie Cups:

  • The cookie part will soften over time as it sits with the filling.
  • The drizzle is optional, but adds another hit of sweetness.
  • These freeze very well! Store in fridge for up to 5 days or in freezer (in an airtight container) for 1-2 months.
  • Best served warm. I recommend microwaving them for 10-15 seconds to heat up!
These Apple Crisp Cookie Cups combine classic oatmeal cookies with homemade apple pie filling for the perfect comfort food. | livforcake.com
4.6 from 15 votes
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Apple Crisp Cookie Cups

These Apple Crisp Cookie Cups combine classic oatmeal cookies with homemade apple pie filling for the perfect comfort food.
Course Dessert
Type Cookie, Tart
Prep Time 1 hour 30 minutes
Cook Time 30 minutes
Total Time 2 hours
Servings 24
Calories 259 kcal
Author Olivia

INGREDIENTS

Apple Pie Filling:

Oatmeal Cookie Cups:

Sugar Glaze:

US Customary - Metric

INSTRUCTIONS

Apple Pie Filling:

  1. Toss apples and lemon juice in a medium bowl, set aside.
  2. In a medium saucepan, combine sugars, cornstarch, and spices. Pour in water. Cook over medium heat until boiling. Cook for 2 minutes. Add apples, bring back to a boil. Simmer until tender (10-15mins). Cool completely.

Oatmeal Cookie Cups:

  1. In a medium bowl, whisk flour, cinnamon, baking soda, and salt. Set aside.
  2. In the bowl of an electric mixer, beat butter and sugars on med-high until pale and fluffy (approx. 3 minutes).
  3. Add eggs one at a time, fully incorporating after each addition, and beat on high for 1 minute. Add vanilla.
  4. Turn mixer to low and add flour mixture, mix until combined. Add oats and mix until just combined.

  5. Spray 2 regular sized muffin tins with cooking spray. Using a large cookie scoop (3 Tbsp) scoop dough into muffin tins, press down and push up the sides to create cups.

  6. Preheat oven to 350°F. Bake cookie cups for approx. 15mins or until browned and mostly set.
  7. Remove from oven and (if needed) immediately use a small jar or container to press firmly down in the center to create a well. Cool in pans for 15mins, then place on wire rack to cool completely.

Assembly:

  1. Using a tablespoon, fill each cookie cup with apple pie filling. Drizzle with sugar glaze if desired.

These Apple Crisp Cookie Cups combine classic oatmeal cookies with homemade apple pie filling for the perfect comfort food. | livforcake.com

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Your favourite chewy oatmeal cookies come together with homemade apple pie filling in these bite-sized Apple Crisp Cookie Cups. | livforcake.com
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The nutritional information and metric conversions are calculated automatically. I cannot guarantee the accuracy of this data. If this important to you, please verify with your favourite nutrition calculator and/or metric conversion tool.

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Comments

  1. What kind of cup do you use to make the well? Someone mentioned about making the well first and then baking them. Did that work. Wouldn’t like to know by Friday if possible that’s the day I plan to try to make them.

    Reply

    • Hi Diane! I used my fingers to mold them before baking and then I used the cap from my Pam for Baking spray to do the indent. Something like a small jar or shot glass will work fine though too.

      Reply

  2. Just made these and took the recommendation to chill the dough and I feel like it helped “set”the dough. These are simply delicious! I will make more for Thanksgiving, thank you for the wonderful recipe.

    Reply

  3. Hi, can I replace flour with all purpose gluten free flour to make the crust? I would loveeee to try this recipe but I would have to change it to GF! Also if I use mini muffin pan (24 cavities per pan) do you have any suggestions to change the temperature or baking time? Thank you so much inadvance for the great recipe!

    Reply

    • Hi Hazel! I think the AP GF flour should work fine. For the smaller pan, keep the oven temp the same but start checking them maybe at 7mins or so? Let me know how they turn out!

      Reply

  4. Hi Olivia The Caramel Apple Oatmeal cookies sound delish! What is the shelf life for them? I bake cookies & brownies for 2 shops near me and I seal them in food grade bags, usually 3 cookies per bag ( bags are 4 3/4″
    x 6 3/4″ 3mil bags) The clientele prefer a soft rather than crunchy cookie. Also what size /weight is each cookie
    approximately? Thanks so much for your reply and TERRIFIC recipes. Susie

    Reply


      • I’ve made them in the MINI pan – Love that size! LOVE the Cookie Cups. I’m making them again for a Desert Party for a friend…cause they are That Good. No Chocolate Chips..don’t need them.
        Think I’ll make the cups ahead of time and filling the day of the party.

        Reply


  6. I just tried these with my kids. Observations: The cookie cup itself is very tasty. We just need to refine the shaping and removing. Ours were too thick on the bottom and too thin on the sides. Several sides cracked off as we removed them. Definitely would chill the dough next time. I’m intrigued by the suggestion to mold them onto the bottom of the muffin tins and may try that next time.

    Reply


  7. 3 tbsp of cookie dough per tin was WAY too much. they all “popped” up and it was messy and not good…I’ve made cookie cups before and this was a nightmare. The apple recipe smells good – but I would just recommend not using 3tbsp 🙂

    Reply

    • Hi Monica, 3Tbsp of cookie dough is the correct amount for a standard cupcake tin, which is what the recipe calls for. Perhaps you used a mini cupcake tin? Sorry it didn’t work out for you!

      Reply

  8. Could you bake the cups on the back side of the muffin tin? The cups would be formed while baking. I’ve never tried this before.

    Reply

    • Hi Kristi! Ideally, yes. Pop them in the fridge if making in advance and take out 1 hour or so before serving. I actually recommend microwaving them for a fresh-out-of-the-oven kinda taste 🙂

      Reply


  10. Made these & they were delicious. Will say they are big & quite filling. Doubled the recipe & got 48 exactly. They were quite time consuming. Took 5 hours but, again, I did make a double batch & I only had 1 pan to use. I did however use a “gold” muffin pan. No spraying & they came right out without any sticking.

    Reply


  11. Made these yesterday and my husband declared they are his new favorite dessert!!! Had a little apple filling left over after filling 24 cups so I saved it to put over morning oatmeal…..SO GOOD!!! Thank you for the great recipe!

    Reply

  12. Hi Olivia! I have my cookie cups in the fridge right now. It made 17 not 24. I used the 3 Tbsp scoop. Anyway, they look good so far 😉. My filling was a bit runny so I heated it up again and added some more cornstarch with water and cooked it some more. I will assemble them tomorrow at my sisters place for Thanksgiving! I can’t wait to try them. I may add a bit of cinnamon to the sugar glaze because I love cinnamon!

    Reply


  13. It took 4 hrs to make 36. They turned out perfect. You need the right cup to press. I used oatmeal raisin pre maid cookie dough. I maid my own apple filling. Topped with Carmel and icing.

    Reply

  14. They look wonderful. I am wondering if they could be made with packaged oatmeal cookie dough. Has
    anyone tried that?

    Reply

  15. Has anyone had trouble removing the cups from the pan once done? I am thinking about making these & I have made similar recipes & even though I thoroughly sprayed the pan my cups stuck & broke when I tried to take them out.

    Reply

    • Hi Elaine! The dough for these is a bit firm due to all the oats, so I hope you don’t have any issues taking them out! My process is typically to press down to make the cups, leave them for 5-10mins, then go around and twist and loosen each one (I mostly just do this to make sure they aren’t stuck), then I leave them in there until they’re stiff enough to remove.

      Reply

    • Me as well. Was wondering if I should have let them cool a bit before of seeing them down. Well.oiled and they all broke and won’t come out 😓

      Reply

      • Hi Richard! Sorry to hear about your troubles with these. Sounds like they were possibly left in the pans too long when cooling. They will start to stick as they cool. Did you try flipping the pan over and whacking it to see if they might pop out?

        Reply


  16. I made these for a appy night we had when we were camping. Everyone loved them. I am making them again today for a family dinner. It’s good to low after reading the comments that they can be frozen. Thanks for sharing this recipe with us.

    Reply

  17. To make the well in the middle, couldn’t you press a second muffin sheet down on top of the hot tin? I haven’t tried it but wondered if that would work?

    Reply

    • Hi Robin! You could try that for sure, though I’m not sure if the sides of the cups would be too thin then (and harder to judge even-ness). Also, with the oatmeal cookie cup specifically, the dough is a bit thick, so you need to press firmly to create the well. I’m not sure how easy it would be with another muffin tin on top, but if you try it, please let me know!

      Reply

  18. Do you think these could work in mini muffin tins? If yes, do you have any suggestions that could help out when making them mini?

    Reply

    • Hi Victoria! They should work just fine in mini muffin tins, though they’d be a bit harder to squish down and couldn’t hold as much filling. I would try using 1 Tbsp of cookie dough per mini muffin tin and see how that ratio is. I used 3Tbsp per regular muffin tin.

      Reply


  21. Hi Olivia, tried this recipe & they tasted delicious. The cookie cups are not too sweet even when I added the chocolate chips. I didn’t prepared the Apple pie fillings but instead opt for a readymade. But none the less they tasted great. Thank you for sharing luv 😘

    Reply

  22. I used the extra filling and blended it in my nutribullet and it’s just like apple butter!! Would recommend if you had extra like me!!

    Reply


  23. I made this while it look very nice and tasted great, I think next time I’ll just make into a bar, I found it very time consuming

    Reply


  24. I made this for my team at work for our bosses last day on our team and everyone loved it! Actually brought cookie ‘cups’ and the filling to work separately, then filled the cups and heated in microwave at work. Was easy to travel with and assemble!

    Suggestion for making cookie cups – chill a bit in muffin tin before pushing up sides, and make sure to push up plenty. I found that couldn’t make much of a well after cooking and had too much extra filling, which is not a bad thing 😉

    Thanks for a great recipe!

    Reply

    • Hi Carolyn! I’m so glad that you and your team loved these! Good call on taking them separately and heating up the filling. Thanks for the tips! 🙂

      Reply

    • Hi Regina! As long as it’s a GF flour blend that replicates regular flour it should work fine. Otherwise you’d need to add a gum of some sort.

      Reply


  26. I just made these. They are quite easy to make. The hardest part was punching down the cookie after coming out of the oven to get a cup. Some were perfect, other not so much. They are cooling right now. My husband just tried one, and he said “it was really good”. High praise from him. They filling is thick but still runny. Not sure if I would put in a lunch box. Maybe it will harden as the apples are still slightly warm. I love the idea of the cookie cup rather than dough. Thank you for the recipe. It is very unique.

    Reply

    • Hi Susan! I’m so glad you liked this recipe! I agree, punching down the cups is the trickiest part, but they don’t all have to be perfect — certainly not all of mine were. I probably wouldn’t toss them into a lunch box without putting them in their own little container, or maybe wrapping them in plastic wrap. They freeze really well, so you could pop a frozen one into a lunch box (wrapped in plastic) and it should thaw out before they need to eat it :).

      Reply

      • Thanks for the tip on freezing them. Another nice thing about the recipe is that is truly makes 24 cookie cups. I often find a recipe will say for example, 24, but actually make 18. Nice to know I can freeze some for later. I have handed out a couple to more. So far, everyone really likes them.

        Reply

      • I used to make tart shells this way: roll out pie crust, cut out circle of dough, drape over the back side of a muffin tin, press gently to form, patch cracks and holes, bake, and repeat. It took hours to make any significant quantity, and I couldn’t bring myself to bother with it more than once a year.

        This life-changing gadget has revolutionized the process. You drop a ball of pie crust into a tart pan or mini muffin pan, dip the wooden end of the tart press/tamper into some flour so it won’t stick, and do a quick little press-and-wiggle maneuver to form beautiful tarts. We made ten or twelve dozen mini tarts for our last party: mini pumpkin pies, chocolate ganache tarts (with chocolate crust), and honey-nut tarts.

        Two hints: If you’re using a mini muffin pan to make tart shells, then one medium cookie scoop (I use the OXO brand scoops) is enough dough for TWO mini tarts. Also, if you roll the ball of dough between your hands, to make it mostly smooth, then you’ll get prettier tarts with smooth, uncracked edges at the top.

        Reply

        • Thanks for the awesome tips, Marie! I don’t make pies and tarts often because of the hassle with the dough, but you have convinced me to check out this tart press! Sounds like a life saver :).

          Reply

  27. Why do people comment without actually making them? That’s not helpful. I look for peoples opinions who actually made them.

    Reply

  30. Actually wanted one of these in my hand right now, they sound incredible! Crunchy oatmeal cookie + warming spiced apple filling? And none of the trials involved with pie crust making? Such a win! So right for the cold weather hitting Melbourne at the moment.

    Reply

    • I know, right?? Pie crusts are my least fave thing ever to make. I am sure they would be perfectly comforting for the Fall weather in Aus! 🙂

      Reply


  33. Who cares if it’s not autumn. I can go for apple desserts anytime – especially when they sound as heavenly as these. I think my kids would be delighted to find one of these in their lunchbox on a Friday as their end of the week treat.

    Reply

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