Woodrow Wilson Trivia
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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 01Which sitting president did Wilson defeat in 1912?
William Howard Taft
William Howard Taft carried only Utah and Vermont as Wilson became the 28th president; nine years later he got the job he had long wanted, Chief Justice of the United States.
Q 02In which Virginia town was Wilson born, in the manse of his father's Presbyterian church?
Staunton
Staunton. As president-elect in 1912 he came back for his 56th birthday and slept two nights in the manse where he was born, now part of his presidential library.
Q 03During World War I, which animals did the Wilsons put on the White House lawn to keep the grass cut?
Sheep
Sheep. The flock saved on manpower in wartime, and its wool was auctioned for the benefit of the Red Cross.
Q 04Besides Wilson, which US president was a citizen of the Confederacy, even winning a seat in its Congress?
John Tyler
John Tyler died in January 1862 before he could take that seat, and the United States government gave the former president's death no official recognition.
Q 05Wilson's 1887 journal article made him a founding father of which academic field?
Public administration
Public administration. His essay 'The Study of Administration' argued that running a government deserved study in its own right, apart from the politics that set its goals.
Q 06Wilson taught at Wesleyan University in Connecticut from 1888, where he also did what for the school?
Coached the football team
Wilson coached the football team and also got Wesleyan students to organise a debating society run as a 'House of Commons'.
Q 07Wilson served as president of which university from 1902 to 1910?
Princeton
Princeton got stiffer standards under Wilson, who hired dozens of young 'preceptors' to guide students in small groups and appointed its first Jewish and first Catholic professors.
Q 08As a university president, Wilson tried and failed to abolish which exclusive student institutions?
The upper-class eating clubs
The upper-class eating clubs were to give way to residential quadrangles shared by all four classes, but furious alumni got Wilson's plan defeated.
Q 09Wilson served as governor of which state before winning the presidency?
New Jersey
New Jersey's Democratic bosses backed Wilson expecting a naive professor they could steer, but he declared his independence at once and pushed through reforms that cut their power.
Q 10Which political machine's backing tainted Wilson's rival Champ Clark at the 1912 convention?
Tammany Hall
Tammany Hall swung New York's votes to Clark and gave him a majority, but the boss backing turned the party's progressives against him, and Wilson finally won on the 46th ballot.
Q 11Which former president ran against Wilson in 1912 as the 'Bull Moose' third-party candidate?
Theodore Roosevelt
Theodore Roosevelt bolted the Republicans after losing their nomination fight, and the split let Wilson carry 40 states.
Q 12Wilson won in 1912 with under 42 percent of the vote, the lowest winning share since which president?
Abraham Lincoln
Abraham Lincoln won a four-way race in 1860 with about 40 percent, and Wilson's share was low for the same reason: his opponents had split a party between them.
Q 13Which Socialist won six percent against Wilson in 1912, his party's highest presidential share?
Eugene V. Debs
Q 21Wilson's first wife Ellen, who had a skylit studio installed at the White House, had trained as what?
A painter
A painter by training, Ellen Wilson kept working as First Lady, and her death in 1914 spurred Congress to pass the slum-housing bill she had campaigned for.
Q 22Which silent epic drew protests after Wilson's White House screening in 1915?
The Birth of a Nation
The Birth of a Nation cast the Ku Klux Klan as heroes, and within months of its release a new Klan, inspired by the film, was founded in Georgia.
Q 23Which Mexican city did Wilson order the Navy to occupy in 1914 after an incident at Tampico?
Veracruz
Eugene V. Debs ran again in 1920 from a federal prison cell in Atlanta, where he was serving ten years for an anti-war speech made during Wilson's presidency.
Q 14Wilson was the first Southerner elected president since which Mexican-American War general won in 1848?
Zachary Taylor
Zachary Taylor was the last until Wilson, whose Southern-born Cabinet members were soon allowed to segregate federal departments such as the Post Office and the Treasury.
Q 15Which legal scholar helped craft Wilson's 'New Freedom' and later became his Supreme Court nominee?
Louis Brandeis
Louis Brandeis's 1916 nomination set off a four-month Senate fight over his attacks on big business and his religion before he became the first Jewish justice.
Q 16Which Wilson Secretary of State resigned in 1915 over the response to a liner sinking?
William Jennings Bryan
William Jennings Bryan quit in June 1915, convinced that Wilson's stern protest notes to Germany would drag the country into an unnecessary war.
Q 17Wilson revived the spoken address to Congress, a custom ended in 1801 by which president?
Thomas Jefferson
Thomas Jefferson sent his messages in writing instead, reportedly because a speech to lawmakers smacked of a king addressing Parliament, and every president followed suit until Wilson in 1913.
Q 18Which institution did Wilson sign into being two days before Christmas 1913?
Federal Reserve
The Federal Reserve was a compromise between private and government control: bankers would run twelve regional reserve banks, but under a board appointed by the president.
Q 19Which watchdog agency did Wilson create in 1914 to police unfair business practices?
Federal Trade Commission
The Federal Trade Commission could investigate and publicise unfair practices, and weeks later the Clayton Act spelled out which ones were banned while shielding unions from antitrust suits.
Q 20The Keating–Owen Act, signed by Wilson, barred goods made with what from interstate trade?
Child labor
Child labor was the target, but the Supreme Court struck the law down in 1918, and a lasting federal ban had to wait for the Fair Labor Standards Act of 1938.
Veracruz was seized within two weeks of the brief arrest of American sailors up the coast, and its loss so weakened General Huerta that he gave up power that July.
Q 24Which revolutionary did Wilson's troops hunt in Mexico after a 1916 border raid?
Pancho Villa
Pancho Villa was never caught: several thousand US soldiers chased him through northern Mexico for months, clashed with Mexican government troops instead and came home empty-handed.
Q 25Which liner's 1915 sinking, killing over a hundred Americans, tested Wilson's neutrality?
RMS Lusitania
RMS Lusitania went down within sight of the Irish coast, and three days later Wilson told a Philadelphia crowd there was such a thing as a man being 'too proud to fight'.
Q 26Which holiday did Wilson make official in 1914, only for its founder to campaign later for its abolition?
Mother's Day
Mother's Day was Anna Jarvis's creation, but she came to loathe the trade in cards and flowers it spawned and spent her later years trying to get it struck from the calendar.
Q 27Edith Wilson claimed descent from which famous Native American woman?
Pocahontas
Pocahontas topped the family tree that Virginia's Bollings prized, yet Edith, the seventh of eleven children in rural Wytheville, had little formal schooling.
Q 28Democrats campaigned for Wilson's 1916 re-election under which slogan?
He Kept Us Out of War
He Kept Us Out of War carried Wilson to a narrow win in November 1916, and five months later he was asking Congress to declare war on Germany.
Q 29Which Supreme Court justice resigned from the bench to run against Wilson in 1916?
Charles Evans Hughes
Charles Evans Hughes gave up a seat for life and lost narrowly, yet he returned to the Court in 1930 as Chief Justice.
Q 30Wilson's 1916 re-election hung for two days on which Western state, which he carried by a sliver?
California
California tipped the election, and Wilson's Republican rival may have thrown it away there by slighting the state's Progressive governor, Hiram Johnson, while campaigning.