Dill Pickle Sloppy Joe Grilled Cheese: The Ultimate Comfort Food Mashup

What happens when you combine a classic Sloppy Joe with a gooey grilled cheese and add a tangy dill pickle twist? You get the most mouthwatering, flavor-packed sandwich ever—the Dill Pickle Sloppy Joe Grilled Cheese!

This cheesy, meaty, saucy sandwich is a game-changer for comfort food lovers. The savory, slightly sweet Sloppy Joe meat is loaded onto buttery grilled bread with melted cheese and crunchy pickles, creating a perfect bite of rich, tangy, cheesy goodness.

Whether you’re making this for a fun dinner, game day, or a comfort food craving, it’s an easy, indulgent, and unforgettable sandwich!

Why You’ll Love This Sloppy Joe Grilled Cheese

✔ Cheesy & Meaty – A perfect balance of rich ground beef and melty cheese.
✔ Sweet, Savory & Tangy – The bold Sloppy Joe sauce pairs perfectly with tangy pickles.
✔ Crunchy & Buttery Bread – Grilled to golden perfection for crispy edges.
✔ Easy & Quick – 30-minute recipe with simple ingredients.
✔ Great for Any Occasion – Perfect for weeknights, game day, or anytime comfort food calls!

The Best Dill Pickle Sloppy Joe Grilled Cheese Recipe

This recipe is a mix of classic Sloppy Joes and grilled cheese, with melted cheddar, tangy pickles, and buttery toasted bread.

Ingredients (Makes 4 Sandwiches)

For the Sloppy Joe Filling:

1 lb ground beef (or ground turkey)
½ small onion, finely diced
2 cloves garlic, minced
½ cup tomato sauce
¼ cup ketchup
1 tablespoon Worcestershire sauce
1 tablespoon brown sugar
1 teaspoon mustard (yellow or Dijon)
½ teaspoon salt
½ teaspoon black pepper
¼ teaspoon smoked paprika (optional, adds a smoky flavor)

For the Sandwich:

8 slices Texas toast or thick sandwich bread
4 tablespoons butter, softened
2 cups shredded cheddar cheese (or slices of cheddar/American cheese)
8-10 slices dill pickles (or more, depending on preference)

Step-by-Step Instructions

1. Make the Sloppy Joe Filling

In a large skillet over medium-high heat, cook ground beef until browned, breaking it apart (about 5 minutes).
Add diced onion and garlic, sautéing until softened (2 minutes).
Stir in tomato sauce, ketchup, Worcestershire sauce, brown sugar, mustard, salt, black pepper, and smoked paprika.
Let simmer for 5 minutes until the sauce thickens.
Remove from heat and set aside.

2. Assemble the Sandwiches

Spread butter on one side of each bread slice.
Place 4 slices (butter-side down) on a clean surface.
Add ½ cup shredded cheddar cheese (or 2 slices) on each bread slice.
Spoon a generous portion of Sloppy Joe filling over the cheese.
Layer with pickle slices.
Add another layer of cheese on top of the pickles.
Top with the remaining bread slices (butter-side up).

3. Grill the Sandwiches

Heat a large skillet or griddle over medium-low heat.
Place sandwiches in the pan and cook for 3-4 minutes per side, pressing lightly with a spatula.
Flip carefully and cook until golden brown and crispy, with cheese fully melted.
Remove from heat and let rest for 1 minute before slicing.

4. Serve & Enjoy!

Cut sandwiches in half and serve immediately.
Pair with extra pickles, coleslaw, or a side of crispy fries!

Tips for the Best Sloppy Joe Grilled Cheese

✅ Use thick bread – Texas toast or sourdough works best for crispy, sturdy sandwiches.
✅ Low & slow grilling – Cooking over medium-low heat ensures perfectly melted cheese without burning the bread.
✅ Don’t skimp on pickles! – The tanginess balances the rich flavors.
✅ Extra saucy? – Add a little more Sloppy Joe sauce before serving.
✅ For a spicy kick – Add sliced jalapeños or a drizzle of hot sauce!

Variations & Customizations

Want to mix it up? Try these fun twists!

1. Spicy Jalapeño Sloppy Joe Grilled Cheese 🔥

🌶 Add sliced jalapeños or a drizzle of hot sauce.
🌶 Use pepper jack cheese for extra heat.

2. BBQ Bacon Sloppy Joe Grilled Cheese 🥓

🍖 Swap ketchup for BBQ sauce.
🍖 Add crispy bacon for a smoky crunch.

3. Buffalo Ranch Sloppy Joe Grilled Cheese 🧀

🌟 Toss the Sloppy Joe meat in Buffalo sauce before assembling.
🌟 Serve with ranch dressing for dipping.

4. Sloppy Joe Patty Melt 🍔

🥩 Swap sandwich bread for rye bread.
🥩 Add caramelized onions for an old-school diner twist.

What to Serve with Sloppy Joe Grilled Cheese

This cheesy, saucy sandwich pairs perfectly with classic sides:

🍟 French Fries or Tater Tots – Because extra crispy goodness is always welcome.
🥗 Coleslaw – A fresh, tangy balance to the richness.
🥒 Extra Dill Pickles – For an extra punch of tang.
🥣 Tomato Soup – A warm, comforting dip for your sandwich.
🍺 Cold Beer or Soda – The perfect refreshing drink pairing.

How to Store & Reheat

Sloppy Joe Grilled Cheese is best served fresh, but you can store leftovers!

Storing:

Keep in an airtight container in the fridge for up to 3 days.

Reheating:

Stovetop: Heat on a skillet over medium-low heat until warm.
Oven: Bake at 350°F (175°C) for 5-10 minutes.
Air Fryer: Reheat at 375°F for 4-5 minutes for a crispy finish.

Final Thoughts: The Ultimate Comfort Sandwich

This Dill Pickle Sloppy Joe Grilled Cheese is a bold, messy, and utterly delicious take on a classic comfort food! It’s cheesy, saucy, tangy, and packed with flavor, making it perfect for game day, family dinners, or anytime you’re craving something indulgent.

🔥 Try it tonight and enjoy the best grilled cheese you’ve ever had! 🔥