Kentucky Derby Inspired: Grilled Ham and Pimento Cheese Sandwiches

We’re making Pimento Cheese because after 4 years of living in New Orleans, I now understand that no Southern gathering is complete without Pimento Cheese spread in one way or another.

This version transforms the spread into the classic comfort of a grilled cheese sandwich. There’s no way to go wrong here! 

Here’s what you’ll need:

• an egregious amount of sharp cheddar cheese.  More is more is more. 

•  cream cheese that’s been softened to room temperature.

•  mayonnaise, yes we’re making Southern food.

• onion, we’ll grate raw onion for a bit of sharp flavor.

•  sweet pimento peppers. 

•  sliced ham and white bread and extra butter for grilling. 

Pimento cheese spread start with a major amount of very sharp cheddar, grated very finely on the skinny side of a box grater.  There’s no cheat here…. just grate it all.  Pro-tip: don’t let anyone hang around who is going to snack on your hard work.  

Gather a good 6 cups of grated cheese into a bowl.  

On the wide side of a box grater, being careful of your fingers, and… admittedly feeling a bit awkward- grate a few tablespoons of raw onion.  

Add the onion bits to the cheese mount and head for the pimento peppers.  We’ll use a lot! From the jar, chop them finely. 

With the main ingredients grated and chopped start with the spread element.  It’s a very romantic blend of cream cheese and mayonnaise. 

Season well with salt and fresh cracked black pepper.  

And spoon the cream cheese mixture onto the mountain of cheese. 

It will feel thick, but stir heartily.  It will break down and come together.  You won’t be able to keep from tasting it… I promise. 

My secret ingredient: smoky paprika.  It adds the most lovely smoky spice!  I love it, just a bit will do. 

That’s it!  Just like that we have pimento cheese spread!

The good news is that this spread is also a dip which means if you have Ritz crackers in your pantry you can sneak yourself a fiiiiine snack. 

Inside of a sandwich, a thing later of this spread makes a fine cheesy base for our sandwich.  Butter one side, pimento spread the other and add a slice of ham! 

Well buttered and ready for grilling!  

Grill until both sides are golden brown and the insides are soft and melty.  

I give the sandwiches at least five minutes before cutting them in half to serve.  

Pairs quite nicely with the Sweet Potato Potato Salad, a room full of rowdy friends, and the most exciting 2 minutes in sports!   

Grilled Ham and Pimento Cheese Sandwiches
Serves 6
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Prep Time
20 min
Cook Time
10 min
Prep Time
20 min
Cook Time
10 min
For the Pimento Cheese
  1. 6 cups finely grated sharp cheddar cheese
  2. 3 tablespoons finely grated yellow onion
  3. 1/2 cup finely diced pickled sweet pimento peppers
  4. 1/2 cup mayonnaise
  5. 4 ounces (half a brick) cream cheese, softened
  6. 1/2 teaspoon sea salt, plus more to taste if you'd like
  7. 1/2 teaspoon fresh cracked black pepper, plus more to taste if you'd like
  8. scant 1/2 teaspoon smoky paprika
For the Sandwiches
  1. 1/2 cup unsalted butter, softened
  2. loaf of sliced white bread
  3. 6 slices of ham
  4. pickles, for serving
  1. In a medium bowl combine the grated cheese, grated onion, and chopped peppers. Set aside.
  2. In a small bowl, whisk together mayonnaise, cream cheese, salt, pepper, and paprika. Mix until thoroughly combined. Taste and season accordingly.
  3. Dollop the mayonnaise mixture over the grated cheese and toss together until well combined. The mixture will be thick. Taste and add more seasoning if you'd like.
  4. Lightly butter one side of all the bread slices. Turn over overthe buttered bread and spread pimento cheese spread across all of the slices. Top 6 of the bread slices with a folded piece of ham. Sandwich together and grill in a nonstick skillet over medium heat until golden brown on each side, melty inside. Enjoy warm!
Joy the Baker