Final answer:
Theodore Roosevelt and his Rough Riders fought at the battle of San Juan Hill during the Spanish-American War.
Step-by-step explanation:
Theodore Roosevelt and his "Rough Riders" fought at the battle of San Juan Hill during the Spanish-American War. The Rough Riders were an all-volunteer cavalry unit, consisting of college graduates, veterans, and cowboys, who charged up Kettle Hill next to San Juan Hill, resulting in the surrounding of Santiago by American forces. This battle was a significant part of the war and Roosevelt's leadership during this charge made him one of the most notable heroes of the war.