The siege of Santiago, also known as the siege of Santiago de Cuba, was the last major operation of the Spanish–American War on the island of Cuba.

The Battle of San Juan Hill, also known as the Battle for the San Juan Heights, was a major battle of the Spanish–American War fought between an American force under the command of William Rufus Shafter and Joseph Wheeler against a Spanish force led by Arsenio Linares y Pombo. The battle proved to be one of the most significant battles of the war and, along with the Siege of Santiago, a decisive battle in deciding the fate of the United States Army campaign in Cuba. The American forces, outnumbering the Spanish defenders 16-to-one, charged upon the heights and dispersed the Spanish after suffering heavy casualties.