Dill Pickle Grilled Cheese

Featured in Stacked sandwiches worth craving.

This sandwich brings two favorites together—grilled cheese loaded with cheddar and a sloppy joe-style mixture packed with tangy pickles. Ground beef, sweetened with brown sugar and ketchup, gets seasoned with savory mustard. Layered on thick-cut toast with chopped dill pickles, it's grilled until crispy on the outside and fluffy inside. Perfectly rich yet balanced by the pickles' zing and crunch, this fusion is as satisfying as it is melty.

alicia in the kitchen
Updated on Tue, 10 Jun 2025 18:22:05 GMT
A cheesy sandwich packed with beef and pickles. Pin it
A cheesy sandwich packed with beef and pickles. | tasteofsavor.com

Get ready for a comfort food mashup that packs a punch. You’ll taste zippy pickles right alongside melty cheese and hearty sloppy joe goodness. It’s tangy, cheesy, a little meaty, and gonna make your tongue happy.

These sandwiches came about back when we were juggling nonstop sports nights. I was trying to use up leftover sloppy joe mix. Now, it’s everyone’s first pick when I ask what we should make for sandwich night. Can’t go wrong.

Bold Ingredients

  • Unsalted butter: Makes the outside crispy and golden—it’s what everyone looks forward to biting into
  • Cheddar cheese: Gives you stretchy, gooey pulls when you tear apart the sandwich
  • Texas Toast bread: Super sturdy, doesn’t get squishy and holds everything together
  • Dill pickles: Add crunch and burst through with tangy flavor that steals the show
  • Black pepper: Sprinkles in gentle heat and a bit of oomph
  • Kosher salt: Brings out the best in all the flavors—go for a chunky kosher salt
  • Brown sugar: Kicks in a soft sweet touch to tame the sharpness
  • Yellow mustard: Brightens everything and balances out the cheesy, meaty bits
  • Ketchup: Sweetens things up in the classic sloppy way
  • Garlic powder: Blends into the meat for all-over flavor with zero burn
  • Sweet onion: Sweetens the mix and levels out any sour notes from the pickles
  • Lean ground beef: Packs in protein and keeps the sandwich from being greasy
  • Extra virgin olive oil: Cooks the beef and onions just right, without weighing down the taste

Simple How-To

Finish with Grilling:
Give the sandwich 1 to 2 minutes on each side in the skillet until golden and crunchy. Flip it gently with a big spatula and squish down just a little, so the cheese melts and holds everything together. Pull it off when the bread is crisp and the inside’s gooey hot. Put it on a cutting board, slice it any way you like, and eat right away.
Put the Sandwich Together:
Wipe out your skillet, then heat it up again. Butter one side of a bread slice and lay it butter-side down. Quickly add a handful of cheese, then spoon a good layer of the warm meat mix over it. Sprinkle on more cheese, then top it with another buttered bread slice, buttered side up this time.
Get That Sloppy Joe Filling Ready:
Clean out the excess grease from the pan after browning the beef and onions. Drop the meat back into the skillet, sprinkle in garlic powder, squeeze in ketchup and mustard, then stir in brown sugar. Mix well and give it a minute to bubble. Toss in salt and pepper. Mix in diced pickles last, spread everything into a bowl, and cover so it stays warm.
Start by Browning:
Drizzle olive oil into a big skillet and warm it up. Toss in beef and onion, smashing up the meat as it cooks. Keep going until no pink shows and onions look see-through—about three minutes. Drain that grease with a colander so your sandwiches aren’t greasy at all.

Honestly, I love how the pickles wake up my taste buds in this. My husband swore he wasn’t into pickles, but now he begs for extras. These are our Friday night thing when football season comes around.

Plan-Ahead Tips

Sloppy joe meat can chill in the fridge up to three days, sealed tight. When you’re ready, just do the grilling—it’s a total timesaver. The filling actually gets richer if it sits for a day or two. Want it long-term? Pop it in freezer containers and stash for up to three months. Just thaw overnight then warm gently on the stove, dash in a little water if you need to loosen it back up.

Easy Personalizations

Tweak this sandwich for your crew. Like it spicy? Add in pepper flakes or hit the meat with hot sauce. Into sweet pickles instead? Swap ‘em for bread and butter style. Don’t have cheddar? Try American, provolone, or pepper jack for some heat or a fancier twist. Feeling lighter? Use ground chicken or turkey—just be sure it’s fully cooked before you load it up.

Serving Pairings

These sandwiches are plenty by themselves, but adding other stuff makes them even better. Grab a handful of potato chips for crunch. Toss a super simple green salad with some tangy dressing to cut the richness. Need something extra? Go for sweet potato fries or dunk it in tomato soup. And if you’re a pickle fanatic, pile some spears on the side, you can’t go wrong.

Frequently Asked Questions

→ Can I try different bread options for this sandwich?

Sure! While thick Texas toast works great, this recipe also pairs with sourdough, brioche, or even rustic artisan bread. Just pick something sturdy enough for the meat and cheese combo.

→ Which cheese melts best for this dish?

You can't go wrong with sharp cheddar as it melts beautifully and has a bold taste. Want variety? American cheese is extra creamy, or go spicy with pepper jack.

→ Can I prepare the meat filling earlier?

Of course! You can whip up the sloppy joe filling a couple of days ahead. Store it in a sealed container in the fridge, then reheat before making your sandwich. It’s a great time-saver!

→ What sides taste great with this sandwich?

Think potato chips, fries, or a crisp salad to balance the richness. Dill pickle spears, coleslaw, or even macaroni salad also pair well for a full meal.

→ How do I keep this sandwich less messy?

Let the meat mixture cool slightly before assembling to thicken it up. While cooking, press down gently to seal the edges, and resting the sandwich briefly before cutting helps everything stick together better.

→ What if I want a vegetarian twist?

No problem! Swap the beef with lentils, crumbled tempeh, or plant-based ground meat. Use the same seasonings for the mixture, and you'll have a satisfying, vegetarian-friendly sandwich.

Dill Pickle Grilled Cheese

A delicious combination of grilled cheese, dill pickles, and sloppy joes for your ultimate hearty treat.

Prep Time
10 Minutes
Cook Time
15 Minutes
Total Time
25 Minutes
By: Alicia

Category: Sandwiches

Difficulty: Easy

Cuisine: American

Yield: 4 Servings (4 cheesy grilled sandwiches)

Dietary: ~

Ingredients

→ Filling for Sloppy Joe

01 2 teaspoons olive oil, extra-virgin
02 1 pound ground beef, lean
03 1 small sweet onion, chopped finely
04 1/2 teaspoon powdered garlic
05 1/2 cup ketchup
06 2 teaspoons mustard (classic yellow)
07 2 teaspoons sugar, brown
08 1/2 teaspoon coarse salt
09 1/4 teaspoon ground black pepper
10 1/2 cup dill pickles, chopped small

→ Putting Together the Sandwich

11 Unsalted butter for cooking
12 2 cups cheddar cheese, shredded
13 8 slices thick-cut bread, such as Texas Toast

Instructions

Step 01

Heat olive oil in a wide skillet over medium-high heat. Toss in ground beef and diced onions. Stir and cook for about 3 minutes, letting the beef brown and the onions soften. Drain off any grease that collects.

Step 02

Add the powdered garlic, ketchup, mustard, and brown sugar to the skillet. Mix everything thoroughly. Sprinkle in salt and pepper, then stir in the chopped dill pickles. Once combined, move the mixture to a bowl, cover it to stay warm, and put it aside.

Step 03

Clean off the skillet and set it back on medium heat. Butter one side of each bread slice. Lay one slice, butter side down, into the pan. Stack some cheese, then add a good amount of sloppy joe filling, more cheese, and top with another slice of bread (butter side up).

Step 04

Cook one side until it’s toasty and golden, which takes about 1 to 2 minutes. Gently flip it over, pressing slightly to melt the cheese. Keep cooking until the second side is golden and all the cheese melts, around another 1 to 2 minutes. Repeat until you’ve made four sandwiches.

Notes

  1. Enjoy right away with pickles or chips for some added crunch.
  2. To make cutting easier and less messy, wait a minute or two before slicing the sandwiches.

Tools You'll Need

  • Wide non-stick skillet
  • Bowl for mixing
  • A spatula

Allergy Information

Please check ingredients for potential allergens and consult a health professional if in doubt.
  • Dairy is included (cheese, butter)
  • Gluten is present (bread)
  • May contain mustard

Nutrition Facts (Per Serving)

It is important to consider this information as approximate and not to use it as definitive health advice.
  • Calories: 680
  • Total Fat: 38 g
  • Total Carbohydrate: 42 g
  • Protein: 35 g