Cheesy Chicken Enchilada Stuffed Squash

Get your Tex-Mex on with these delicious cheesy chicken enchilada stuffed squash bowls! They’re full of fiesta flavor and make the most delicious leftovers!

Cheesy Chicken Enchilada Stuffed Squash

Since boycotting pumpkin this year, I stepped up my squash game.

Er… let me rephrase that so I sound less moronic, since pumpkin is technically a squash too!

I benched pumpkin and brought my favorite over-looked and under-loved squash all-stars out to play the field. They’re seriously rocking my plate and I’m certain you’re going to love them too! It’s safe to say that I’m one proud couch. I mean cook! I mean… Oy, just eat your veggies will ya?

In other news, I think my brain is broken.

I’ve never been a huge fan of squash [Though I said the same for sweet potatoes a few years back and look at me now! Hah!] mainly because any time I tried it, that poor veggie had been manhandled and mistreated into a mushy, soggy, and/or sweetened state. With the right cooking techniques and the right add-ons, it’s downright delicious! A little roasting and some savory side-kicks can take squash from meh to MEEEEEE-OWW!

And with that, my brain finally broke.

Cheesy Chicken Enchilada Stuffed Squash

Cheesy Chicken Enchilada Stuffed Squash

Since Winter squash finally hit the shelves, I’ve been hoarding dumpling squash. Have you had it before? It’s actually the perfect squash for people who don’t like squash! It has the buttery texture and facade of an acorn squash but the mild, easy to compliment flavor of yellow squash and spaghetti squash. It’s not too sweet or too strong or too anything, as Goldilocks would say, this one is juuuuust right!

Can you tell I’ve been reading more baby books than big girl books as of lately? Yeah. Sorry about that.

Let’s get squashed! (again!)

Cheesy Chicken Enchilada Stuffed Squash

1 vote


Cheesy Chicken Enchilada Stuffed Squash

Yield 2-4 servings

Get your Tex-Mex on with these delicious cheesy chicken enchilada stuffed squash bowls! They're full of fiesta flavor and make the most delicious leftovers!


  • 1 dumpling squash
  • 1/2-1 lb boneless, skinless chicken breast (1-2 cups cooked)
  • 1/2 cup salsa verde 
  • 1/8 tsp garlic powder
  • a pinch of cumin
  • salt and pepper, to taste
  • 1 tsp butter or oil for sauteing
  • 1/2-1 cup diced tri-colored bell peppers
  • 1/4 cup diced red onion
  • 2-4 oz freshly grated cheese


  • plain greek yogurt or sour cream
  • chopped green onion
  • am optional pinch of red pepper flakes for added heat
  • diced jalapenos for even more heat! [also yummy; also optional]
  • fresh cilantro

note: Any cheese that rocks your tastebuds will rock this dish! My favorites lately have been gouda and pepper jack yogurt cheese. The yogurt cheese is usually in the fancy cheese section and goes on sale often! It's delicious! Have some of your favorite enchilada sauce handy? Go ahead and add it to the mix!


  1. Pre-heat oven to 400 degrees F.
  2. Mental prep: though this dish has a few components that are all cooked differently, don't fret! You can cook the chicken while the squash roasts and the veggies while the chicken poaches and, before you know it, the kitchen will be clean and you'll have food in your face. Ready? Let's do this!
  3. Slice your squash in half lengthwise and scoop out the seeds.
  4. To prevent sticking, rub the rim of the squash's flesh with a teeny bit of olive oil or simply place a little water inside your baking dish. Both work great!
  5. Place inside a baking dish or atop rimmed, lined baking sheet [some liquid will escape] and roast face-down for approx 40 minutes.
  6. While the squash roasts, cook your chicken and saute your veggies.
  7. You can cook the chicken any which way you prefer but to save on time I typically crock-pot it ahead of time [see notes in the post below] or throw it together on the stove top while the squash bakes away.
  8. Bring a medium pot of water or your favorite broth [hello flavor!] to boil and add your boneless, skinless chicken breasts to the water.
  9. Cover your pot with it's lid and remove from heat.
  10. Allow the chicken to poach for approx 25 minutes.
  11. Remove from liquid, chop with the grain into small pieces and combine with salsa verde.
  12. Season with salt and pepper [cayenne pepper if you're feeling spicy!] as well as your garlic powder and cumin.
  13. Stir and set aside.
  14. As mentioned earlier, while the chicken cooks, saute those veggies!
  15. Simply bring a little bit of butter or oil to heat, add your peppers and onion and saute until tender.
  16. By now you should have a kitchen full of yum!
  17. Rake a fork across the bottom of the squash and stir in your salsa chicken, peppers, and onion.
  18. Top with a mountain of freshly grated cheese and pop squash back in the oven for a few minutes to melt the cheese.
  19. Serve bubbly and hot with all your favorite toppings!

sassy shortcuts

If your kitchen happens to be overrun leftovers from a festive Taco Tuesday the night before, or any night of the week really, then you can whip this dish up with little to no effort! That’s actually how I created this baby in the first place! Of course other ways to shave time off this recipe would be to bake your squash ahead of time, when you know you’ll be around to yank it from the oven when the timer goes off. It’ll stay fresh in your fridge for a few days awaiting this delish dish.

You can also cook the chicken in advance on the stove top, in the oven, or using your slow cooker! I love making a huge batch of salsa shredded chicken over the weekend to toss into meals all week long. It’s easy and requires so little effort that it’s become a go-to these past few months. Simply season the chicken with a little salt, cumin, and garlic powder, pour over your favorite salsa verde, and let your crock-pot do the work! It can be ready in 3-4 hours on high or 6-8 hours on low; choose what works for you!

Another quick fix? Use leftover roast chicken or snag a rotisserie at the supermarket on your way home for work and have at it! With so many delicious possibilities for this recipe, you’re sure to enjoy it every which way!

update: the squash can also be microwaved for 5 minutes, halved, and then roasted at 400 F for 15-20 minutes! I tried this method the other day and it worked great!!!

but really . . . how was it?!

Despite the fact that it I over-explained the crap out of this recipe, it’s so ridiculously easy and awesome and, well, you’ve got to try it! It’s a fiesta in a (squash) bowl! I positively love it and have made it a few more times since posting it. I’ll never tire of this one!

:: pin it for later ::


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  • Marlene

    Possibly a dumb question – but are we cooking the chicken BEFORE poaching? I’m thinking not, but step 7 talks about cooking the chicken and then step 8 talks about poaching in boiling water/broth so I wasn’t sure…

    Looks AMAZING. Thanks!!

    • Jenn

      I get overly descriptive with recipes from time to time since many have so much flexibility to them! This one in particular I will often make a huge batch of chicken in the crock pot for ahead of time since it will keep in the fridge for 4 days and I can add it into all sorts of recipes throughout the week [squash one day, quesadillas the next, stuffed sweet potatoes and so forth!] so I mentioned that fact if anyone wanted to plan ahead. For anyone making the recipe in a sitting, poaching is the quickest method to cook the chicken so when I’m making the recipe start to finish, I’ll do that! It’s flexible any which way you prefer it! =) Hope that helps Marlene and I hope you try it out soon! Keep me posted! xoxo

  • I’ve never heard of a dumpling squash but I must find them! This looks fantastic.

  • ooey gooey cheesy goodness!!

  • So glad you’re boycotting pumpkin…I’m already over it 😉

    Looks delish, thanks!

  • This looks so delicious! As soon as this came into my email, we pretty much went out to buy a dumpling squash. We made your CHEESY PESTO CHICKEN LASAGNA STUFFED SPAGHETTI SQUASH this past week and it was amazing so I’m not worried about this at all. I can’t wait!

    Thanks for the great recipes!


  • I love the mental prep. People read long lists and freak out, but it’s really easy stuff to do at once! I’m with you! 🙂

  • You are crazy for boycotting pumpkin!! But this recipe looks DEEEEELICIOUS!

  • Looks good! Will have to try this since my usual baked-squash-as-a-side-dish gets a bit dull.

  • Holy crap that just looks heavenly! I’ve never heard of dumpling squash, but I’m definitely going to keep my eyes out for it now. Yum!

  • This looks so beautiful and I’ll bet it tastes even better. Can’t wait to try it! I’m already thinking that Habanero Cheddar would make this muy bueno!

    • Jenn

      YES! YES! 1000X YES! That’s my favorite cheese =)

  • Keep the squash love coming because I’ve got a basement full of them. For real, I’ve got a spaghetti squash, an acorn, some butternuts and we’re just getting started with the squash season. I am not a huge squash is the best thing ever type girl, so I’m incredibly grateful for recipes (like this one) which actually make it look like something I would enjoy. Pinned it, and as soon as I’m done with the greens, I shall make this.

    • Jenn

      You have to make it! You’re my official recipe tester!

  • This looks AMAZING! I’ve never seen that squash in my store though – I’m gonna have to look around!

    • Jenn

      Thanks Amanda! It’s usually by the fancy gourds or nestled next to the acorn squash. It’s worth hunting down; the mild, buttery flavor is fantastic!

  • i wish I could find squash over at my supermarket!! I absolutely LOVE the cheese stuffing though. Everything is better with cheese 😀

    • Jenn

      Your supermarket doesn’t sell squash!? ahhh I hope they start carrying it soon! Farmers markets maybe?

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