| 1856 | Woodrow Wilson is born on December 28 in Staunton, Virginia, to Joseph Ruggles Wilson and Jessie Janet Woodrow. |
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| 1875 | Wilson enrolls at the College of New Jersey (later renamed Princeton University). |
| 1885 | Wilson earns his Ph.D. in political science from Johns Hopkins University. |
| 1902 | Wilson becomes the president of Princeton University, serving until 1910. |
| 1910 | Woodrow Wilson is elected Governor of New Jersey, serving until 1913. |
| 1912 | Wilson is elected as the 28th President of the United States, defeating incumbent President William Howard Taft and former President Theodore Roosevelt. |
| 1914 |
July 28. World War I begins in Europe. October 15. Wilson signs the Clayton Antitrust Act, strengthening the federal government’s ability to regulate monopolies and protect consumers. |
| 1916 | Woodrow Wilson is reelected as President of the United States, defeating Republican Charles Evans Hughes. His campaign slogan is “He kept us out of war.” |
| 1917 |
April 6. The United States declares war on Germany, entering World War I on the side of the Allies. December 26. Wilson nationalizes the U.S. railroad system to support the war effort. |
| 1918 | January 8. Wilson delivers his famous Fourteen Points speech, outlining his vision for a lasting peace after World War I. |
| 1919 |
June 28. The Treaty of Versailles is signed, ending World War I. Wilson’s League of Nations is included as a key component of the treaty. October 2. Wilson suffers a severe stroke, leaving him partially paralyzed and significantly limiting his ability to govern. |
| 1920 |
March 19. The U.S. Senate rejects the Treaty of Versailles for the second time, and the United States never joins the League of Nations. November 2. Wilson’s term as president ends, and Warren G. Harding is elected as his successor. |
| 1921 | Woodrow Wilson retires from public life and moves to a home in Washington, D.C., where he continues to write and give occasional speeches. |
| 1924 | February 3. Woodrow Wilson dies at his home in Washington, D.C., at the age of 67. |