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Winston Churchill Quizzes, Trivia and Puzzles
Winston Churchill Quizzes, Trivia

Winston Churchill Trivia

Winston Churchill Trivia Quizzes

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8 Winston Churchill quizzes and 100 Winston Churchill trivia questions.
  Great Political Speeches: Winston Churchill   best quiz  
Fun Fill-It
 15 Qns
Winston Churchill was a master orator and the speeches he gave in the early days of his Prime Ministership were among his finest hours. Fill in the blanks and feel inspired.
Easier, 15 Qns, Snowman, Jan 17 24
Snowman gold member
Jan 17 24
146 plays
  20 Questions about Winston Churchill   best quiz  
Multiple Choice
 20 Qns
Here are 20 multiple-choice questions about this very interesting British Prime Minister, who guided Britain through the dark days of World War II.
Average, 20 Qns, root17, Apr 13 22
root17 gold member
Apr 13 22
1259 plays
Winston and Clementine Churchill  A Love Story Behind every great man is a great woman and many people agree that it was his finest hour when Winston Churchill married Clementine Hozier. Let us find out a little more about their life together.
Average, 10 Qns, Plodd, Dec 31 16
252 plays
  The Life and Times of Sir Winston Churchill   great trivia quiz  
Multiple Choice
 10 Qns
Sir Winston Churchill is perhaps the most eminent British prime minister of all time. This quiz will test your knowledge, and hopefully provide an interesting insight into this great man.
Average, 10 Qns, delboy22, Jun 07 17
Jun 07 17
1341 plays
  Winston Churchill   top quiz  
Multiple Choice
 10 Qns
Probably no other past British Prime Minister is more widely admired than Churchill, so it is more than a little surprising that this is the first Funtrivia quiz on him.
Tough, 10 Qns, bloomsby, Oct 19 19
bloomsby gold member
Oct 19 19
1501 plays
  Winston Churchill Quotes   top quiz  
Multiple Choice
 15 Qns
Churchill could always be relied on for a good quote. Following is a short quiz on some of his famous - and infamous - utterances.
Tough, 15 Qns, jeffa, Jul 02 07
1584 plays
  The Last Lion: Winston Churchill   top quiz  
Multiple Choice
 10 Qns
10 questions about one of the most fascinating leaders of the 20th Century.
Average, 10 Qns, IgnatiusReilly, Dec 01 17
Dec 01 17
834 plays
  The Failures of Winston Churchill   top quiz  
Multiple Choice
 10 Qns
Winston Churchill did not consult focus groups or polls. He often did not even consult leaders of his party. But many of these actions show a foresight and purpose that is beyond the vision of others. They show the values and integrity of a statesman.
Average, 10 Qns, PALSC, Oct 06 10
278 plays
trivia question Quick Question
Where did Churchill continue his education after leaving Harrow?

From Quiz "Winston Churchill"

Winston Churchill Trivia Questions

1. Winston's father, Lord Randolph Churchill, was British. What nationality was his mother, born Jeanette "Jennie" Jerome?

From Quiz
20 Questions about Winston Churchill

Answer: American

Both his parents led very busy lives, and young Winston was primarily raised by devoted nanny Mrs. Everest (he called her "Woomany" or "Old Woom"). By all accounts she was a kind and good woman, and is sometimes referred to as "the nanny who saved western civilization." Years later, addressing the U.S. Congress, Churchill said, "By the way, I cannot help reflecting that if my father had been American and my mother British, instead of the other way around, I might have got here on my own."

2. In which building was Churchill born?

From Quiz The Last Lion: Winston Churchill

Answer: Blenheim Palace

Winston came into the world eight months after his parents married. You do the math. One of the largest houses in England (located in Woodstock, Oxfordshire), much of Blenheim Palace is open to the public although the 11th Duke of Marlborough retains ownership. Winston's grandfather, John Spencer-Churchill, was the 7th Duke of Marlborough.

3. In which county was Sir Winston Churchill born?

From Quiz The Life and Times of Sir Winston Churchill

Answer: Oxfordshire

Sir Winston was born at Blenheim Palace, Oxfordshire, on 30 November 1874. He was the elder of two sons.

4. Where and when was Winston Churchill born?

From Quiz Winston Churchill

Answer: Woodstock, Oxfordshire: 1874

He was born in Blenheim Palace, the family seat of the Duke of Marlborough, on 30 November 1874. His father, Lord Randolph Churchill, who was active in politics, was a younger son of the duke; his mother, Jeanette (Jennie) Churchill, née Jerome, was originally American.

5. Which political rival did Churchill call 'A sheep in sheep's clothing' and 'A modest little man, with much to be modest about'?

From Quiz Winston Churchill Quotes

Answer: Clement Attlee

Clement Attlee (1883-1967) was the leader of the Labour Party during World War II, and succeeded Churchill as Prime Minister in 1945. His deceptively mild exterior hid a strong character, and he was not afraid to have a go at Churchill, for example, 'I must remind the right honourable gentleman that a monologue is not a decision.'

6. What military academy did Winston Churchill attend?

From Quiz 20 Questions about Winston Churchill

Answer: Sandhurst

All three wrong answers are military academies located in the US. Some of his lead soldier collection is displayed at Sandhurst, which is in the English county of Berkshire.

7. Churchill's father, Lord Randolph, was English. In which country was Churchill's mother born?

From Quiz The Last Lion: Winston Churchill

Answer: USA

His mother, Jennie Jerome, was born in Brooklyn and one of many American women to marry in to British aristocracy near the end of the 19th Century. According to her biographer Anne Sebba, Jennie's father was a speculator who lost fortunes as fast as he made them. Marrying Lord Randolph provided financial security.

8. In what subject did Sir Winston Churchill win a Nobel prize in 1953?

From Quiz The Life and Times of Sir Winston Churchill

Answer: Literature

Churchill's literary career began with campaign reports. He wrote The Story of the Malakand Field Force in 1898, and The River War in 1899, which was an account of the campaign in the Sudan and the Battle of Omdurman. In 1900, he published his only novel, Savrola. This was followed six years later with his first major work, the biography of his father, Lord Randolph Churchill. His other famous biography, the life of his great ancestor, the Duke of Marlborough, was published in four volumes between 1933 and 1938.

9. Where did Churchill continue his education after leaving Harrow?

From Quiz Winston Churchill

Answer: Royal Military Academy, Sandhurst

Churchill was one of the minority of British prime ministers who didn't go to Oxford or Cambridge. Instead, he trained as an army officer, fought in the the North-West Frontier Province (in what is now Pakistan) and in the Sudan, and he wrote about these campaigns. In the Boer War he was a war correspondent for the "Morning Post", was captured and imprisoned by the Boers but succeeded in escaping. On his return to Britain he found that he had become something of a national hero.

10. With whom did Churchill have the following famous exchange: 'If you were my husband, I'd put poison in your coffee.' 'If you were my wife, I'd drink it.'

From Quiz Winston Churchill Quotes

Answer: Nancy Astor

Nancy Astor (1879-1964) became the first female Member of Parliament when she was elected as MP for Plymouth in 1919. She had the odd verbal spat with Churchill, and when he once asked her advice on a fancy dress costume, she suggested, 'Why don't you come sober, Mr. Prime Minister?'

11. What was the first name of Winston Churchill's wife? (Hint: He was married to only one woman his entire life.)

From Quiz 20 Questions about Winston Churchill

Answer: Clementine

They were married 57 years. In his letters to her, he called her "Clemmie". Her advice to him on social and political matters often influenced what he said and did.

12. How many of the four Great Offices of State did Churchill hold during his life?

From Quiz The Last Lion: Winston Churchill

Answer: 3

He was Home Secretary, Chancellor of the Exchequer, and Prime Minister. The fourth Great Office is Foreign Secretary.

13. When did Churchill first become a Member of Parliament?

From Quiz Winston Churchill

Answer: 1900

In 1900 he was elected as the Conservative MP for Oldham, but he switched to the Liberal Party in 1904. He was a Member of Parliament continuously from 1900-22 and 1924-64.

14. What was the name of the country estate purchased by Churchill?

From Quiz 20 Questions about Winston Churchill

Answer: Chartwell

All three wrong answers are the homes of former U.S. presidents. Churchill bought Chartwell, located two miles south of Westerham, Kent, England, for £5,000 in 1922. He fell in love with the place when he first saw it (not so much for the house, but for the views of the Kent countryside), and put in a purchase offer without Clementine's prior approval. Chartwell would be WC's home until his death in 1965. It is presently under the administration of the National Trust, and is now open to the public. Historical note: Monticello was the home of Thomas Jefferson (third U.S. president). Montpelier was the home of James Madison (fourth U.S. president). Sagamore Hill was the home of Theodore "Teddy" Roosevelt (26th U.S. president).

15. In 1914, as First Lord of the Admiralty, Churchill went to Antwerp, which was rumoured to be ready to surrender to the Germans. He called for reinforcements to hold Antwerp. As a result, what happened?

From Quiz The Failures of Winston Churchill

Answer: Antwerp fell 1 week later, And 2,500 troops were lost.

Antwerp fell after a week, and Churchill was blamed for squandering resources. However, the delay allowed the transfer of more troops to reinforce Calais and Dunkirk.

16. To what political party or parties did Churchill belong?

From Quiz The Last Lion: Winston Churchill

Answer: Conservative and Liberal

He was a member of the Conservative Party from 1900-1904, the Liberal Party from 1904-1924, and returned to the Conservative Party from 1924-1964. In Churchill's own words upon returning to the Conservatives: "Anyone can rat, but it takes a certain amount of ingenuity to re-rat."

17. In 1904, which political party did Churchill leave, and which party did he join?

From Quiz The Life and Times of Sir Winston Churchill

Answer: Conservative to Liberal

In 1900, Churchill became Conservative member of parliament for Oldham. But he became disaffected with his party and in 1904 joined the Liberal Party. When the Liberals later won the election, Churchill was appointed under-secretary at the Colonial Office.

18. In what war was Churchill taken prisoner and then escaped? (Hint: The reward poster after his escape noted, "He does not speak a word of Dutch.")

From Quiz 20 Questions about Winston Churchill

Answer: Second Boer War

This war was during 1899-1902 between the British Empire and the Dutch settlers (Boers) of the area north-east of what is now South Africa (the First Boer War was 1880-1881). Churchill went there as a war correspondent for the Morning Post newspaper, and jumped at the chance to take a train into the action. He was captured by the Boers, and even though he was a fairly insignificant 25-year-old civilian, he was from an influential family and the Boers thought he could be a good bargaining chip. However, he escaped and made his way back to the British lines. This escape was widely publicized back in England and helped launch his political career.

19. In 1914, while First Lord of the Admiralty, Churchill proposed a campaign to open another front in the war, that would force attention away from the trench warfare that was killing so many soldiers. Where was this campaign?

From Quiz The Failures of Winston Churchill

Answer: Dardanelles

The action was a disaster for diplomatic and strategic reasons. Churchill was forced to resign. In 1917, he was cleared of any blame in the Dardanelles disaster.

20. To which World War Two leader was Churchill related?

From Quiz The Last Lion: Winston Churchill

Answer: Franklin Roosevelt

Winston Churchill and FDR were seventh cousins once removed on FDR's mother's side.

21. Which government post did Churchill hold between 1924 and 1929?

From Quiz The Life and Times of Sir Winston Churchill

Answer: Chancellor of the Exchequer

During World War One, Churchill joined the army, serving for a time on the Western Front. In 1917, he was back in government as Minister of Munitions. From 1919 to 1921 he was Secretary of State for War and Air, and from 1924 to 1929 was Chancellor of the Exchequer.

22. 'If Hitler invaded hell, I should at least make a favourable reference to the devil in the House of Commons'. On what occasion did Churchill say thist?

From Quiz Winston Churchill Quotes

Answer: The Nazi invasion of the Soviet Union

Churchill, a long-standing and rumbustious opponent of Communism, extended the USSR considerable aid during the war. He famously described Russia as '... a riddle wrapped in a mystery inside an enigma.'.

23. What was Churchill's speech impediment? (Hint: He used to practice saying, "The Spanish ships I cannot see for they are not in sight.")

From Quiz 20 Questions about Winston Churchill

Answer: Pronounced "S" as "Sh"

He was afraid his speech impediment would hinder his political career, but it has become almost an endearing quality of his speeches. Winston's father, Lord Randolph Churchill, also had a speech impediment.

24. After resigning as First Lord of the Admiralty, Churchill asked for a military field command. He was given the position of lieutenant colonel in the Royal Scots Fusiliers. What role did he have the rest of the war?

From Quiz The Failures of Winston Churchill

Answer: Served beside his men on the Western Front, 1916.

Churchill was not welcomed into the army after the incident at the Dardanelles. After serving, Churchill's men said there was no better loved commander on the Western Front.

25. From 1929 to 1939, Churchill was effectively out of politics. What expression is commonly used to describe these years?

From Quiz The Last Lion: Winston Churchill

Answer: The Wilderness Years

When Prime Minister Ramsay MacDonald formed the National Government in 1931, Churchill was not invited to join the Cabinet. He supported himself by writing during this time and was quite successful, as his Nobel Prize demonstrates.

26. Which government post did Churchill take upon the outbreak of war in 1939?

From Quiz The Life and Times of Sir Winston Churchill

Answer: First Lord of the Admiralty

When war broke out in 1939, Churchill became First Lord of the Admiralty. In May 1940, Neville Chamberlain resigned as Prime Minister and Churchill took his place. His refusal to surrender to Nazi Germany inspired the country. He worked tirelessly throughout the war, building strong relations with US President Roosevelt while maintaining a sometimes difficult alliance with the Soviet Union.

27. 'A ___________ is one who can't change his mind and won't change the subject.'

From Quiz Winston Churchill Quotes

Answer: fanatic

28. What was the name of the British Prime Minister WC replaced just after WWII started? (Hint: "Peace in our time.")

From Quiz 20 Questions about Winston Churchill

Answer: Neville Chamberlain

The widely-known photograph of Neville Chamberlain shows him just after he returned from the Munich Conference in 1938 (in which he agreed no military intervention if Hitler annexed part of Czechoslovakia), waving the document and proclaiming it meant "peace in our time." Historical note: As difficult as it may be to believe, both Chamberlain and Hitler were nominated for the Nobel Peace Prize in 1939 (although nobody won that year). After Hitler invaded Poland on 1 September 1939, even Chamberlain's supporters realized his appeasement foreign policy was wrong and WC replaced him as Prime Minister (although Chamberlain did remain Prime Minister for the first eight months of WWII).

29. During World War I, Churchill championed the development of a new weapon of war that was to be instrumental in fighting trench warfare. What was this weapon?

From Quiz The Failures of Winston Churchill

Answer: Armored tank

Churchill was head of the Land-ships Committee responsible for the development of the First Tank Corps. After he left the Admiralty, a poorly designed field trial was made of the tank and it was dropped. Churchill was blamed for misappropriation of funds. He was reappointed First Lord of the Admiralty on the day Britain declared war on Germany in WW2. The Navy sent word to the ships at sea, "Winston is Back!" The tank became a major weapon in WW2.

30. Churchill was notable for accomplishing something no other Prime Minister had ever done. What was it?

From Quiz The Last Lion: Winston Churchill

Answer: Win a Nobel Prize.

He won a Nobel Prize for Literature. His 1953 Nobel citation reads in part: "...for his mastery of historical and biographical description as well as for brilliant oratory in defending exalted human values."

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