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The expression Cuban sandwich designates, in Cuban-American cuisine, a type of sandwich consisting of a long crusty roll filled with ham, pork, cheese, pickles and mustard, often toasted.

This expression occurs, for example, in the following from Local Flavor on Wheels: Highland Square Food Truck Festival, by Kerry Clawson, published in the Akron Beacon Journal (Akron, Ohio, USA) of Sunday 1^st June 2025 [page 9D, column 4]:

Steve checked out Off the Griddle of Cleveland for his entree, which was a Cuban sandwich. This nontraditional spin on the pulled pork, ham and Swiss cheese sandwich had shredded Swiss and was on pita bread.
“The pickles are nice and crisp,” he said of his sandwich, which was drizzled in mustard.

These are, in chronological order, the earliest occurrences of the expression Cuban sandwich that I have found:
—Note: In early use, this expression designated, more generally, any of various types of sandwich associated with Cuban cuisine:

1-: From the following paragraph, published in the Daily Missoulian (Missoula, Montana, USA) of Tuesday 26^th July 1898 [page 4, column 2]—here, the appellation Cuban sandwich is obviously facetious:

The Cuban sandwich, two hardtack and a bean, are not served at pink teas and other functions even by the most patriotic American women.

2-: From Our Flag Raised on Morro Castle, a correspondence from Camp Columbia, Havana, Cuba, by A. C. Pridgen, Co. G. 4 Va., published in The Record (Warrenton, North Carolina, USA) of Friday 3^rd February 1899 [page 4, column 3]—here, there is no indication of what Cuban sandwich designates:

At 7:30 o’clock on the morning of Jan. 1st 1899, the different regiments were being formed, and twenty-five rounds of amunition [sic] were being issued to every man with which to protect American rights, and to sustain peace and serenity during the day. At 8 o’clock we were on the march to Morro Castle of the city of Havana.
[…] Very frequently the boys would stop and pay respect to their canteens of coffee. After we reached the North side of the city, we halted to take a rest and eat our little Cuban sandwich. As we lounged upon the grass and rocks, we could see far ahead upon the spires of Morro Castle the Spanish flag, which was soon to come down.

3-: From Scenes in Cuba, by ‘G. S.’, published in The Marion Daily Chronicle (Marion, Indiana, USA) of Wednesday 8^th March 1899 [page 5, column 4]:

There are many butchers’ stalls, there are places where greasy cakes, crulls and pastries are spread, and there are guava jelly and brittle rolls that form the Cuban sandwich. As the ham filled article is one of our national institutions, so the jelly-spread biscuit, a loaf baked in green leaves, is one of Cuba’s prides.

4-: From The Times (Richmond, Virginia, USA) of Sunday 21^st October 1900 [page 15, column 4]:

A Cuban Sandwich.

A sandwich popular at Cuban restaurants is almost a meal in itself. It is made with two thin slices of the ordinary wheat loaf made in sandwich form, says the New York Evening Post. No butter is used, but on the lower slice is placed, first, a layer of the breast of cold chicken cut very thin; over this goes more wafer-thin slices of cold boiled ham, then cucumber pickles also sliced very thin; shavings of bologna sausage top the pickle, and over the sausage slices of cheese. The bread top is then put on and the whole is fitted into an oblong frame which neatly and quickly trims off the crust and shapes the sandwich. It is then folded in plain white paper and delivered, the whole operation having been accomplished in sight of the purchaser and in an incredibly short space of time. Twenty cents of our money pays for the sandwich, which is eaten with a glass of wine or of beer.

5-: From Havana’s Hotels and Cafes, a special correspondence from Havana, dated Thursday 8^th January 1903, by Dorothy Stanhope, published in The New York Times (New York City, New York, USA) of Sunday 18^th January 1903 [page 26, column 6]:

On the counters of restaurants are all kinds of baked meats and fowl. The hams are all spiced. Sandwiches are piled up high, but they are not the kind we know, with a simple layer of meat, or nuts, or lettuce. The Cuban sandwich is made of a roll and has three or four things between the sides. The kind known as “medianoche,” suggesting that it is usually eaten late at night, is of a very delicious roll, with chicken and bits of pickle between the sides. Ham, cheese, and pickle are the ordinary filling for a native sandwich.

6-: From Afternoon Tea Dainties, published in The Leader. A Weekly Journal of News, Politics, Agriculture, Sport, Mining, Science, and Literature (Melbourne, Victoria, Australia) of Saturday 8^th August 1903 [page 38, column 5]:

Cuban Sandwich.—Cut slices of very thin bread and butter, spread half the slices with a layer of fresh cream cheese, and on it a layer of chopped dates. On the other side spread chopped burnt almonds. Put the two parts together, stamp into fancy shapes, and serve on a dainty doyley.