- 25-September-1900 : In the British general election, the recentlyrecentlyformed Labour Party gains two seats. Winston Churchill is elected to Parliament for the first time.
- 14-July-1940 : Winston Churchill, in a worldwide broadcast, proclaims the intention of Great Britain to fight alone against Germany whatever the outcome: "We shall seek no terms. We shall tolerate no parley. We may show mercy. We shall ask none."
- 23-December-1940 : Winston Churchill, in a broadcast address to the people of Italy, squarely blames Benito Mussolini for leading his nation to war against the British, contrary to Italy's historic friendship with them.
- 09-February-1941 : Winston Churchill, in a worldwide broadcast, pleads with the United States to show its support by sending arms to the British: "Give us the tools, and we will finish the job."
- 22-June-1941 : War II: Winston Churchill promises all possible British assistance to the Soviet Union in a worldwide broadcast: "Any man or state who fights against Nazidom will have our aid. Any man or state who marches with Hitler is our foe."
- 09-August-1941 : Franklin D. Roosevelt and Winston Churchill meet at Argentia, Newfoundland and Labrador. The Atlantic Charter is created as a result.
- 10-November-1941 : In a speech at the Mansion House in London, Winston Churchill promises, "should the United States become involved in war with Japan, the British declaration will follow within the hour."
- 26-December-1941 : War II: Winston Churchill becomes the first British Prime Minister to address a joint session of the U.S. Congress.
- 14-January-1943 : Franklin D. Roosevelt becomes the first President of the United States to travel by airplane while in office (Miami, Florida to Morocco to meet with Winston Churchill to discuss World War II).
- 12-May-1943 : The Trident Conference begins in Washington, D.C., with Franklin D. Roosevelt and Winston Churchill taking part.