Grilled Cheese Sloppy Joes

Introduction

If you’ve ever had trouble deciding between a sloppy joe and a grilled cheese sandwich, this recipe ends the debate. These Grilled Cheese Sloppy Joes combine the savory, sweet, tangy beef filling of a classic sloppy joe with the buttery, golden crispness of grilled cheese. Each bite delivers a melty cheddar hug around the saucy beef—comfort food turned up to the max. Perfect for weeknight dinners, game nights, or when you want a fun twist on two all-time favorites.

Prep Time: 10 minutes

Cook Time: 20 minutes

Total Time: 30 minutes

Servings: 4 sandwiches

Ingredients

For the Sloppy Joe Filling

1 lb (450g) ground beef

1 small onion, diced

1 small green bell pepper, diced (optional)

2 cloves garlic, minced

3/4 cup ketchup

2 tbsp brown sugar

1 tbsp Worcestershire sauce

1 tsp yellow mustard

1/2 tsp chili powder (optional, for a little heat)

Salt & pepper to taste

For the Grilled Cheese Sandwiches

8 slices thick sandwich bread (white or sourdough work great)

8 slices cheddar cheese (or a mix of cheddar and mozzarella for stretch)

4 tbsp butter, softened

Instructions

Make the Sloppy Joe Filling (12–15 minutes)

In a large skillet over medium-high heat, cook ground beef, onion, and bell pepper until beef is browned and vegetables are softened (about 6–7 minutes).

Drain excess grease.

Add garlic and cook for 30 seconds until fragrant.

Stir in ketchup, brown sugar, Worcestershire sauce, mustard, chili powder, salt, and pepper.

Reduce heat to low and simmer for 5–6 minutes, stirring occasionally, until thickened.

Assemble the Sandwiches (3 minutes)

Lay out bread slices and butter one side of each slice.

Place 1 slice of cheese (butter side down) in a skillet, top with a scoop of sloppy joe mixture, add another slice of cheese, then top with bread (butter side up).

Grill to Golden Perfection (4–5 minutes)

Heat a skillet or griddle over medium heat.

Cook sandwiches for 2–3 minutes per side, pressing gently with a spatula, until bread is golden and cheese is fully melted.

Slice in half and serve immediately.

Tips for Best Results

For ultra-cheesy sandwiches, use 3 slices of cheese per sandwich—one under, one over the meat, and one in between.

If your sloppy joe mix is too saucy, let it simmer a bit longer to avoid soggy bread.

Try Texas toast for thicker, crunchier results.

For spice lovers, add diced jalapeños or a splash of hot sauce to the meat mixture.

Serving Suggestion

Serve with a side of fries, pickles, or a simple green salad to balance the richness.