Lieutenant-Colonel Henry Norlande Ruttan, who came from the Retired List, commanded the regiment on organization (General Order No.

[2][4][5] Details from the 100th Winnipeg Grenadiers were placed on active service on 6 August 1914 for local protection duties.

It was redesigned as the 11th Reserve Infantry Battalion, CEF, on 29 April 1915 to reinforce the Canadian Corps in the field.

[2][4] The 78th Battalion (Winnipeg Grenadiers), CEF, was authorized on 10 July 1915 and embarked for Great Britain on 20 May 1916, disembarking in France on 13 August 1916, where it fought as part of the 12th Canadian Brigade, 4th Canadian Division in France and Flanders until the end of the war.

[2][4] Ethelbert "Curley" Christian (-15 March 1954) of the 78th Battalion, Winnipeg Grenadiers was wounded at the Battle of Vimy Ridge and was the only quadruple amputee of either World War to survive.The regiment mobilized The Winnipeg Grenadiers (Machine Gun), CASF, on 1 September 1939.

It served in Jamaica and at the Imperial fortress colony of Bermuda (home base of the America and West Indies Station of the Royal Navy, with a military garrison that had been part of that of Nova Scotia, the second nearest landfall from Bermuda after the United States, under the Commander-in-Chief, Maritime provinces 'til Bermuda and Newfoundland, both having been parts of British North America,[6][7] were left out of the 1867 Confederation of Canada, and which had been garrisoned during the First World War successively by the Royal Canadian Regiment, and the 38th Battalion (Ottawa) and 163rd Battalion (French-Canadian) of the Canadian Expeditionary Force (CEF))[8][9][10][11][12][13] on garrison duty from May 1940 to October 1941 (the detachment assigned to the Bermuda Garrison moved to Aruba in August 1940).

[16] His Victoria Cross citation reads, in part: The enemy threw a grenade which landed in a position where it was impossible to pick it up and return it in time.

Shouting a warning to his comrades, this gallant Warrant Officer threw himself on the grenade, which exploded, killing him instantly.

Company Sergeant-Major Osborn was an inspiring example throughout the defence, which he assisted so magnificently in maintaining against an overwhelming enemy force for over eight and a half hours, and in his death, he displayed the highest quality of heroism and self-sacrifice.The 1st Battalion was reconstituted on 10 January 1942.

It took part in the expedition to Kiska, Alaska, as a component of the 13th Canadian Infantry Brigade Group, serving there from 16 August 1943 to 22 December 1943.

[2][4]On 15 August 1914, an alliance was authorized with the Prince of Wales's Leinster Regiment (Royal Canadians).

In 1946 members of the regiment through the Grenadiers Winnipeg Incorporated took steps to reform the cadet corps.