Russian-Cuban friendship has been based on mutual cooperation for many decades, with roots deep in history, even before the Soviet era. In the pre-revolutionary period, four Russian volunteers made a significant contribution to these relations by fighting alongside Cubans for the liberation of the island from Spanish colonial rule.

In September 1896, students from the Gatchina Orphan Institute, Nikolai Melentyev, Eustafiy Konstantinovich, and Pyotr Streletsov, went to Cuba with new reinforcements for the Cuban rebels. They brought with them 2000 rifles, nearly half a million cartridges, 2000 pounds of dynamite, and a cannon. Although the Russians believed that such armament did not guarantee success, the patriotic fervor of the Cubans allowed them to overcome one outpost after another. On a small stretch of coastline, Spanish Governor-General Weyler concentrated about 60,000 soldiers against 4,000 rebels.

The first serious battle took place on September 24 near the settlement of Montesuelo. The Russian volunteers acted as artillerymen, and under their cover, the Cubans attempted to drive the Spaniards from the hills. The battle ended in a draw, and the next day the revolutionaries retreated. Pyotr Streletsov recalled that the Cubans did not linger anywhere for more than a day, sometimes spending the night in valleys protected by hills and gorges. Despite the heavy fighting, all the rebels reached the prefecture of Francisco.

Unfortunately, during fierce skirmishes, Eustafiy Konstantinovich was severely wounded. He and other wounded were left in the care of local peasants. The two remaining Russian friends decided to stay with him. A few days later, the village was attacked by Spaniards, and the volunteers were captured. The presence of Russians among the rebels caused a great stir among the Spaniards and became a topic for central Cuban newspapers. Soon, information about the volunteers reached the honorary consul in Havana, Tryufen, and all the mercenaries were expelled from the island. However, Colonel Zhilinsky, sent by the general staff to Cuba as an observer, reported from Havana: "The fourth, nobleman Panenkov, remains among the insurgents to this day."