60 free Woodrow Wilson trivia questions with answers — history quiz, new questions added Aug 2026.
This Woodrow Wilson trivia quiz follows the 28th president from a Presbyterian manse in Staunton, Virginia, through Princeton, the New Jersey governorship, two terms in the White House and the stroke that left his wife quietly running the executive branch. The easy questions cover the basics: his party, the war he led America into, the peace organisation he championed and the prize it won him. The harder end is for history buffs: the 46-ballot convention that nominated him, why he only needed 41.8 percent of the vote to win, the first Jewish Supreme Court justice he appointed, the telegram that pushed America into the war, the propaganda office he created, the Volstead veto Congress overrode, and the unusual honour of being the only president buried in Washington, D.C. There are also questions on both First Ladies, the Palmer Raids, his record on segregation, and the 1944 Hollywood biopic that lost Fox a fortune. Every answer was checked against encyclopaedia entries for Wilson, the 1912 and 1916 elections, the Fourteen Points, the Zimmermann Telegram and related topics before publishing, and the supporting sentence is stored with each question. If you enjoy this one, our US Presidents, World War I and Teddy Roosevelt quizzes are natural next stops.
30 of 60 questions with answers and explanations. Play the quiz
Q 01Woodrow Wilson was which number president of the United States?
28th
He served two full terms and was the only Democrat to hold the office during the Progressive Era.
Q 02In which Virginia town was Wilson born, in the manse of his father's Presbyterian church?
Staunton
His family moved to Augusta, Georgia before he was two, and his earliest memory was hearing that Lincoln's election meant war.
Q 03Wilson is the only US president to hold which academic credential?
A PhD
Johns Hopkins awarded it in 1886 for work that became his book Congressional Government, which one critic ranked with the Federalist Papers.
Q 04Wilson was one of only two US presidents to have been citizens of the Confederacy; who was the other?
John Tyler
Wilson's father was a founder of the Southern Presbyterian church and a staunch Confederate supporter during the war.
Q 05Wilson's 1887 journal article made him a founding father of which academic field?
Public administration
The article argued that administrators should be a separate profession, accountable to elected leaders who answer to the people.
Q 06Wilson taught at Wesleyan University in Connecticut from 1888, where he also did what for the school?
Coached the football team
As an undergraduate he had been secretary of the football association and president of the baseball association.
Q 07Wilson served as president of which university from 1902 to 1910?
Princeton
He tried to replace the 'gentleman's C' with serious study and appointed the university's first Jewish and first Roman Catholic faculty members.
Q 08As a university president, Wilson's failed attempt to curb social elites targeted which institutions?
The upper-class eating clubs
He wanted students housed in quadrangle colleges instead, but alumni fought the plan fiercely.
Q 09Wilson served as governor of which state before winning the presidency?
New Jersey
In office he broke with the party bosses who had picked him and signed antitrust laws known as the 'Seven Sisters'.
Q 10At the 1912 Democratic convention, Wilson finally secured the nomination on which ballot?
46th
Front-runner Champ Clark faded after Bryan refused to back any candidate supported by Tammany Hall.
Q 11Which former president ran against Wilson in 1912 as the 'Bull Moose' third-party candidate?
Theodore Roosevelt
The Republican split let Wilson carry 40 states with just 41.8 percent of the popular vote.
Q 12Wilson won the 1912 election with what share of the popular vote, the lowest for a winner since 1860?
41.8%
He nonetheless became the first candidate ever to top 400 electoral votes, and the only one to do so without a popular majority.
Q 13Socialist Eugene V. Debs won what record share of the popular vote against Wilson in 1912?
6%
It remains the best showing by a Socialist candidate in any American presidential election.
Q 21Wilson's first wife Ellen Axson Wilson, who died in the White House in 1914, had trained as what?
A painter
She studied at the Art Students League of New York, won a medal at the 1878 Paris Exposition, and learned German to help translate his research.
Q 22Which pro-Ku Klux Klan 1915 film was screened at the White House during Wilson's presidency?
The Birth of a Nation
Historians have since documented his administration's escalation of segregation in government offices.
Q 23Which Mexican city did Wilson order the Navy to occupy in 1914 after an incident at Tampico?
Veracruz
The trigger was the arrest of US sailors who had accidentally landed in a restricted zone.
Q 14Wilson was the first Southerner elected president since which 1848 winner?
Zachary Taylor
Southern segregationists celebrated his victory, and his administration went on to segregate federal offices.
Q 15Which legal scholar helped craft Wilson's 'New Freedom' and later became his Supreme Court nominee?
Louis Brandeis
His 1916 nomination sparked a Senate fight over his progressive views and his religion; he was the first Jewish nominee to the Court.
Q 16Which Wilson Secretary of State resigned in 1915 over the response to a liner sinking?
William Jennings Bryan
The three-time presidential nominee felt Wilson had put American trade rights ahead of true neutrality.
Q 17Wilson addressed a joint session of Congress in person, the first president to do so since whom?
John Adams
Introducing a full domestic agenda at the start of an administration was itself something no president had done before.
Q 18Wilson signed the Federal Reserve Act into law on December 23 of which year?
1913
Congressman Carter Glass and Senator Robert Owen carried the bill that created twelve regional reserve banks.
Q 19Which 1914 act created a new antitrust agency independent of the Justice Department?
Federal Trade Commission Act
One month later Wilson signed the Clayton Act, which defined and banned specific anti-competitive practices.
Q 20The 1916 Keating–Owen Act, passed with Wilson's belated support, restricted what?
Child labor
Wilson had thought such a law unconstitutional but reversed himself with a close election looming.
Q 24Which revolutionary did Pershing hunt in Mexico in 1916 after a raid on Columbus?
Pancho Villa
Wilson had once described him as 'a sort of Robin Hood'; Pershing dispersed his bands but never caught him.
Q 25A German submarine sank which British liner in May 1915, killing 128 Americans?
RMS Lusitania
Wilson demanded Germany prevent any recurrence, and afterwards committed himself to the 'preparedness movement'.
Q 26Wilson met his second wife, Edith Bolling Galt, in March 1915. What was her late first husband's trade?
Jeweler
She rebuffed the president at first, but they were engaged by September and married that December.
Q 27Edith Wilson claimed descent from which famous Native American woman?
Pocahontas
Through her father she was also related to Thomas Jefferson, Martha Washington and Letitia Tyler.
Q 28Democrats campaigned for Wilson's 1916 re-election under which slogan?
He Kept Us Out of War
They warned a Republican win would mean war with Germany; five months after the inauguration the US was at war anyway.
Q 29Wilson's 1916 opponent Charles Evans Hughes remains the only person to have done what?
Served on the Supreme Court and later been a major party nominee
Wilson beat him by fewer than 600,000 votes out of about 18.5 million cast.
Q 30The 1916 election came down to which tipping-point state, which Wilson won narrowly?
California
Nationally Wilson took 277 electoral votes to Hughes's 254.