The 27th Battalion (City of Winnipeg), CEF was an infantry battalion of the Canadian Expeditionary Force during the First World War. 

The battalion was authorized on 7 November 1914 and embarked for Great Britain on 17 May 1915. It disembarked in France on 18 September 1915, where it fought as part of the 6th Infantry Brigade, 2nd Canadian Division in France and Flanders until the end of the war. The battalion was disbanded on 15 September 1920.

The 27th Battalion recruited in Brandon, Portage la Prairie and Winnipeg, Manitoba and Kenora and Rainy River, Ontario and was mobilized at Winnipeg.

Two members of the 27th Battalion were awarded the Victoria Cross :

• Lt. Robert Grierson Combe was posthumously awarded the Victoria Cross for his actions near Acheville, France on 3 May 1917. 

• Pte. James Peter Robertson was posthumously awarded the Victoria Cross for his actions at Passchendaele on 6 November 1917.