Multiple choice Where was the first battle of the Spanish American war fought? San Juan Hill, Puerto Rico The U.S. San Juan Hill, Cuba Manila Bay, Phillipines Reveal answer Fill a bubble to check yourself D Correct answer Explanation The first major military engagement of the Spanish-American War occurred in the Philippines, where Commodore George Dewey destroyed the Spanish fleet in Manila Bay. This was a naval battle, not a land battle like San Juan Hill.