Pepperoni Pizza Grilled Cheese Sandwich

A pepperoni pizza grilled cheese! A great variation on a grilled cheese sandwich with all the ingredients of your favorite pizza.
Did you know that April is National Grilled Cheese Month and the 12th is Grilled Cheese Day? I didn’t until I started seeing dozens of grilled cheese recipes popping up on food blogs all across the internet. So, of course, I had to jump right into that celebration!

I mean, seriously, who doesn’t love a great grilled cheese sandwich? All that warm, melty, gooey cheese and crispy, buttery bread. Yum. But I didn’t want to do just any old grilled cheese. It had to be something really special.
I kept thinking about ways to put a new twist on the classic grilled cheese. I had loads of ideas but this one just kept coming back to mind. A grilled cheese sandwich with all the things we love about our favorite pizza. Tons of pepperoni with lots of mozzarella and black olives. Exactly the way we like our pizzas around here. And, for a little something extra, I made up a compound butter with Parmesan and oregano for the grilling.
Serve these pepperoni pizza grilled cheese sandwiches with a side salad and you have a complete meal. I think you’re really going to like this one!
How to Make Pepperoni Pizza Grilled Cheese
I always start my grilled cheese sandwiches on the stove top but finish them in the oven. I’ve always had a tendency to get the bread too brown before the cheese really melts. Using this method I can grill the bread first and then pop the skillet into the oven to finish melting the cheese.
So, start by preheating your oven to 325 degrees. Then make your compound butter.

Combine the softened butter, Parmesan cheese, and oregano in a small bowl. Stir together until thoroughly combined. Set the butter aside for now.

For these sandwiches, I used a hearty Italian whole grain bread and a firm mozzarella. I thought a fresh mozzarella would be too wet. The firmer, drier mozzarella was a good choice.

Assemble your sandwiches – Spoon a little pizza sauce on both sides of the bread. Top with slices of mozzarella, black olives, and as much pepperoni as you want! I chose a very thinly sliced pepperoni from the deli counter and really piled it up on the sandwiches.
Add the top slice of bread and generously slather it with the compound butter.

Place the sandwiches buttered side down in a skillet (I used cast-iron) over medium heat. Cook until the bread is lightly toasted.
While the first side toasts, butter the second side. Flip the sandwiches and cook the second side.
Transfer the skillet to the oven to finish cooking. Watch carefully and remove when the cheese begins to melt. It takes about 5 to 6 minutes.
🧾 More Recipes You’ll Like
- Easy Pepperoni Pizza Crescent Rolls
- Roasted Tomato Sandwich
- Steak Sandwich
- Hot Roast Beef Sandwiches with Horseradish Cream
- Italian Sausage and Roasted Pepper Sandwich
- Mediterranean Pressed Sandwich
HAVE YOU TRIED THIS RECIPE?
I’d LOVE to know what you thought!
Leave a rating below in the comments and let me know how you liked it!
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Pepperoni Pizza Grilled Cheese
Ingredients
For the compound butter:
- 4 tablespoons softened butter
- 3 tablespoons grated Parmesan cheese
- 1 teaspoon dried oregano
- dash of salt
For the sandwiches:
- 4 slices whole wheat bread
- 4 tablespoons prepared pizza sauce
- 4 ounces sliced or grated mozzarella cheese
- 2 tablespoons sliced black olives
- 4 ounces thinly sliced pepperoni
Instructions
- Combine all ingredients for the compound butter in a small bowl. Stir until thoroughly combined.
- Assemble the sandwiches: For each sandwich, spread a small amount of pizza sauce on the surface of two slices of bread. On the bottom slice, add the mozzarella cheese, black olives, and pepperoni. Top with second slice of bread.
- Spread the top of the assembled sandwiches with a generous amount of compound butter. Place the sandwiches, buttered side down in a skillet over medium-high heat. Cook until bread is nicely grilled. While the first side is grilling, butter the second side of the sandwich. Turn sandwiches over and cook until the second side is toasted.
- Place skillet with sandwiches in preheated oven for 5-6 minutes or until the cheese is melted.Remove from oven and serve immediately.
Notes
Nutrition Information
Nutrition information is calculated by software based on the ingredients in each recipe. It is an estimate only and is provided for informational purposes. You should consult your health care provider or a registered dietitian if precise nutrition calculations are needed for health reasons.
More Grilled Cheese Sandwiches …
- Garlic Naan Grilled Cheese from Half Baked Harvest
- Spinach Artichoke Grilled Cheese from A Couple Cooks
- Grilled Cheese Sandwich with Bacon and Pear from Simply Recipes
- Mini Grilled Cheeses from Love and Lemons
I, too, used this recipe as the basis for the sandwich I made for the May Crazy Cooking Challenge- -http://momscrazycooking.blogspot.com/. I really love your idea for finishing these up in the oven. You have some wonderful sounding recipes here, and I am now following by email. Thanks for sharing.
I just made this grilled cheese the other day and the family loved it! Thanks for sharing! I used this great recipe for the crazy cooking challenge for May at Moms Crazy Cooking @ http://momscrazycooking.blogspot.com/
I am printing out this recipe for my boys to make while I am gone – they love grilled cheese and will absolutely adore this sandwich!! Fabulous idea Lana!!
Hope they like it, Nancy! We really loved it. Tastes just like pepperoni pizza so what’s not to like, right :-)
Hubba Hubba!
What a fantastic way to enjoy grilled cheese! This is so creative, Lana. Thanks for sharing!
I really like the idea of the compound butter-I’ve made zillions of grilled cheese, but that never occurred to me. Great idea! Oh, and pepperoni and mozz are two of my favorite food groups.
Mmm, I love grilled cheese! I’ve never thought about putting pepperoni on it, but this sounds amazing! Pizza grilled cheese…I can get behind that.
Hi Lana, I just came from Triber and saw your post. I’ve been looking for a twist on grilled cheese and I think this is just what I’m looking for. Thanks so much for sharing this.
Joanne
You’re welcome! Enjoy!
Want it!!!
Miss P
These were really very, very good. You should try them!
I can always eat a grilled cheese like this. Yum!