February 15, 1898 · Cuba Theater

The USS Maine, an American battleship anchored in Havana Harbor to protect American interests during the Cuban revolt against Spain, was destroyed by a massive explosion on the evening of February 15, 1898. Two hundred and sixty-six sailors and officers were killed. The cause of the explosion has never been definitively established — naval investigations at the time blamed an external mine, while later studies suggest an internal magazine accident — but the disaster was immediately seized upon by the American press, particularly William Randolph Hearst's New York Journal, as evidence of Spanish treachery.

May 1, 1898 · Philippines Theater

In the predawn hours of May 1, 1898, Commodore George Dewey led the Asiatic Squadron of six warships into Manila Bay in the Philippines and proceeded to systematically destroy the Spanish Pacific Fleet. Dewey's modern steel warships faced an outmatched Spanish fleet of wooden and obsolete vessels under Rear Admiral Patricio Montojo. Dewey famously told his flagship captain, 'You may fire when you are ready, Gridley,' and within hours the entire Spanish fleet of ten ships was sunk, beached, or burning. The Americans suffered only nine wounded — not a single man killed in combat.

June 10, 1898 · Cuba Theater

The Battle of Guantánamo Bay was the first significant land engagement of the war, fought between June 6 and 17, 1898, as U.S. Marines under Lieutenant Colonel Robert Huntington seized and held a coaling station to support the naval blockade of Cuba. The Marines landed at Guantánamo Bay and fought off several Spanish counterattacks over multiple days in dense jungle terrain. War correspondent Stephen Crane, covering the battle, wrote vividly of the fighting. Cuban guerrillas allied with the Americans played a crucial role in the final assault that silenced the Spanish wells and broke the enemy's will to hold the area.

July 1, 1898 · Cuba Theater

El Caney was a small fortified village on the heights northeast of Santiago de Cuba, held by approximately 520 Spanish soldiers under the determined General Joaquín Vara de Rey. American planners believed it would fall in two hours; it held out for nearly ten. Brigadier General Henry Lawton's division of 6,600 men assaulted the stone fort, stone church, and blockhouse network throughout the blazing July day. Vara de Rey was mortally wounded rallying his men and died the following day. Even American officers who had opposed him expressed admiration for the defense. The village finally fell late in the afternoon, hours behind schedule.

July 1, 1898 · Cuba Theater

The Battle of San Juan Heights on July 1, 1898 was the bloodiest and most celebrated engagement of the Cuban campaign. The assault comprised two simultaneous charges: the regular infantry against the fortified San Juan Hill itself, and the Rough Riders — the 1st United States Volunteer Cavalry — against the adjacent Kettle Hill. Lieutenant Colonel Theodore Roosevelt, whose superior was incapacitated, personally led the charge up Kettle Hill on horseback, then dismounted and led a second charge toward San Juan Hill. The fighting was brutal, and American forces suffered nearly 1,400 casualties in the day's assaults across the San Juan Heights. African American Buffalo Soldiers of the 9th and 10th Cavalry played a decisive role in the assaults, though they would receive far less recognition than the Rough Riders.

July 3, 1898 · Cuba Theater

With Santiago's landward defenses crumbling after the fall of the San Juan Heights, Spanish Admiral Pascual Cervera y Topete received orders to attempt a breakout from Santiago Harbor rather than surrender his fleet intact. On the morning of July 3, 1898, the Spanish fleet of four armored cruisers and two destroyers steamed out of the harbor entrance in line ahead. The waiting American fleet pounced. In a running battle lasting less than four hours along the Cuban coast, all six Spanish warships were sunk or beached. Admiral Cervera himself was rescued from the sea by American sailors and treated with great honor as a prisoner. American losses were one killed and one wounded.

July 17, 1898 · Cuba Theater

After the destruction of Cervera's fleet and the seizure of the San Juan Heights, Santiago de Cuba was encircled and its garrison of 11,000 men was cut off from resupply. General Shafter conducted negotiations while his army — wracked by yellow fever, malaria, and dysentery — struggled to maintain its siege lines. Disease was a more dangerous enemy than any Spanish soldier: thousands of American troops fell ill in the fetid Cuban summer. General José Toral, after receiving permission from Madrid to negotiate, finally surrendered the city and his entire 24,000-man command (including troops from the surrounding province) on July 17.

July 28, 1898 · Puerto Rico Theater

With Cuba's fate sealed, the United States opened a second front in Puerto Rico. On July 25, 1898, General Nelson Miles landed troops at Guánica on Puerto Rico's southern coast, and three days later American forces entered Ponce — the island's second largest city and its main commercial port — essentially without a fight. The local population was divided: some Puerto Ricans, hoping for independence or autonomy, welcomed American forces; others remained loyal to Spain. The Spanish garrison offered minimal resistance, and the city was occupied bloodlessly, with the American flag raised over the city hall.

August 9, 1898 · Puerto Rico Theater

The Battle of Coamo was one of the most tactically interesting engagements of the Puerto Rico campaign. Brigadier General James Wilson planned a double envelopment of the Spanish defensive position at Coamo, a mountain town in the island's interior. While a frontal force fixed the Spanish defenders' attention, a flanking column swung around through the hills to cut off their retreat. The maneuver worked almost perfectly. The Spanish garrison was surprised, their line of retreat cut, and the town fell quickly. The action demonstrated the improving tactical skill of American volunteer forces over the course of the brief campaign.

August 12, 1898 · Cuba Theater

The naval engagement at Manzanillo on Cuba's southern coast was one of several small actions fought as American naval forces systematically destroyed Spanish gunboats and coastal defenses around Cuba. American warships and converted yachts attacked the harbor at Manzanillo, engaging Spanish gunboats and shore batteries. The action took place on the same day the armistice protocol was signed in Washington, making it among the final combat actions of the war — though word of the ceasefire had not yet reached the combatants. Several Spanish gunboats were sunk or damaged.

August 13, 1898 · Philippines Theater

The fall of Manila on August 13, 1898 was one of the most peculiar engagements in military history — a prearranged surrender designed to exclude Filipino forces from entering the city. Governor-General Fermín Jáudenes, facing both Dewey's fleet in the bay and Filipino insurgents under Emilio Aguinaldo surrounding the city on land, secretly negotiated with the Americans: he would offer token resistance and then surrender to U.S. forces, provided the Filipinos were kept out. The Americans agreed. On the morning of August 13, the mock battle was fought, the Spanish flag was struck, and Manila fell. Crucially, the armistice ending the war had been signed the previous day in Washington — but the telegram had not yet arrived.