| 1895-98 |
Twenty-seven clandestine gun running expeditions sailed from Tampa to Cuba.
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| 1897 |
Spanish General Valeriano Weyler y Nicolau placed an embargo on all shipments of Cuban tobacco to the United States.
Mascotte and Olivette, steamships from the Plant Line, are dispatched to Havana to beat the embargo deadline.
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| 1898 |
February 15 – U.S.S. Maine ordered to Havana, Cuba to protect Americans, exploded in Havana Harbor, killing 260 sailors. The cause of the explosion is still questioned. March 22 – Henry Plant writes to Secretary of War Russell Alger to point out the importance of defending Tampa. Plant suggested Egmont and Mullett Keys were good sites for coastal defense positions.
March 25 – Secretary Alger orders the Chief of Engineers to plan on defenses for the two sites.
April 14 – Tampa is selected, along with Mobile, Alabama and New Orleans, Louisiana, as a mobilization point for United States troops. Tampa is also chosen as the supply base for a possible operation in Cuba.
April 20 – The United States Congress passes a joint resolution against Spain, recognizing Cuban independence.
April 25 – President William McKinley declares war.
May – Troops pour into Tampa, filling the first en-campment at Tampa Heights, spilling over into camps at DeSoto Park, Palmetto Beach, Fort Brooke, Port Tampa, Ybor City, and a park which stood to the west of the Tampa Bay Hotel. By June, 25,000 troops were garrisoned at the various encampments in and around Tampa.
June 1 – The Rough Riders cavalry unit, led by Colonel Leonard Wood and his second in command, Lieutenant Colonel Theodore Roosevelt, arrive in Tampa.
June-August – Major General William Rufus Shafter, a Civil War veteran, directs the war from his "cockpit" at the Tampa Bay Hotel.
July-August – Two women correspondents, Kathleen Blake Watkins, from Toronto Mail and Express, and Anna Northend Benjamin, a 24 year old writer for Look magazine, left Tampa for Santiago, Cuba.
August 12 – Armistice signed with Spain.
December 10 – Treaty of Paris signed, formally ending the war.
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