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| 1899, Oct. 29 |
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| South African (Boer) War (See 1899–1902). The first Canadian contingent was sent to South Africa; a second was sent in 1900. The official contingents were withdrawn before the end of the war, owing to dissatisfaction in Quebec. | 1 |
| Nova Scotia Steel and Coal Corporation (Scotia) and Dominion Iron and Steel Corporation (Disco) emerged as major corporations. | 2 |
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| 1902, Oct. 31 |
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| Cable from Vancouver to Brisbane was completed. | 3 |
| The Trades and Labor Congress expelled a union connected to the Knights of Labor and the American Federation of Labor. Expelled unions formed the National Trades and Labour Congress of Canada. An estimated 155,000 Canadians belonged to labor unions by World War I. | 4 |
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| 1903 |
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| Alaskan boundary arbitration with the United States (See Jan. 24). High dissatisfaction with the award. | 5 |
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| 1904, Sept. 26 |
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| Earl Grey appointed governor-general (1904–11). | 6 |
| Socialist Party of Canada organized. | 7 |
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| 1905, Sept. 1 |
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| Formation of the provinces of Alberta and Saskatchewan. | 8 |
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| 1905–6 |
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| Niagara Falls was developed for hydroelectric purposes for the first time. Ontario Hydroelectric Commission was formed. | 9 |
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| 1908 |
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| Civil Service Commission was appointed for the selection of civil officials. | 10 |
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| 1910 |
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| Formation of a small Canadian navy. | 11 |
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| 1911, Jan. 26 |
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| Publication of a reciprocity agreement with the United States; ratified by the U.S. Senate (July 22). But in the general elections (Sept. 21), the Liberals were defeated on the issue, and reciprocity was dropped. Mr. (later Sir) Robert L. Borden formed a Conservative ministry (Oct. 10). | 12 |
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| March 21 |
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| Duke of Connaught was appointed governor-general (1911–16). | 13 |
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