1892 - At the age of thirteen he published his first newspaper.
1904 - Formed Royal Securities Corporation and he became a minority shareholder and the firm's general manager.
- John F. Stairs' unexpected early death in late September led to Aitken acquiring control of the company.
1906 - On 29th of January in Halifax, he married Gladys Henderson Drury, daughter of Major General Charles Drury.
1910 - Became Unionist Member of Parliament for Ashton Under Lyne, and where he bought and later sold control of the Rolls-Royce automobile company and began to build a London newspaper empire.
1911 - Knighted by King George V. During World War I, the Canadian government put him in charge of creating the Canadian War Records Office in London.