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The two battles fought by the Rough Riders that occurred nearer Santiago Harbor were San Juan Hill and El Caney. Both battles took place during the Spanish-American War in July 1898 and were crucial to the U.S. campaign to capture Santiago. El Caney was fought on July 1, while San Juan Hill, which followed shortly after, was pivotal for securing control over the strategic positions surrounding the city. Their proximity to Santiago Harbor made these battles significant in the overall military strategy of the war.

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