Winnipeg's pre-WW2 skyscrapers (9+ stories only), all buildings are 35 metres or taller, the minimum height for a high-rise according to Emporis:
Union Bank Building (1904) 10 stories
Source: Manitoba Historical Society,
http://www.mhs.mb.ca/docs/sites/unionbankbuilding.shtml
Somerset Building (first seven stories in 1906, two story addition in ~1912) 9 stories
Source: Now Winnipeg,
http://now.winnipeg.ca/images/south-portage
Eaton's Department Store (first five stories in 1905, with additions until 1908) 9 stories including display floor
Source: The Department Store Museum
http://www.thedepartmentstoremuseum....ba-canada.html
Grain Exchange Building (1908, with multiple additions in the decade after) 10 stories
Source: Manitoba Historical Society,
http://www.mhs.mb.ca/docs/sites/grai...building.shtml
McArthur/Childs Building (1909-1988) 12 stories
Source: Manitoba Historical Society,
http://www.mhs.mb.ca/docs/sites/mcarthurbuilding.shtml
Sterling Building (1912) 9 stories
Source: Now Winnipeg,
http://now.winnipeg.ca/resources/ima...-bank-building
Boyd Building (1912) 9 stories
Source: Manitoba Historical Society,
http://www.mhs.mb.ca/docs/sites/boydbuilding.shtml
Lindsay Building (1912) 10 stories
Source: Manitoba Historical Society,
http://www.mhs.mb.ca/docs/sites/lindsaybuilding.shtml
Confederation Building (1912) 10 stories
Source: Manitoba Historical Society,
http://www.mhs.mb.ca/docs/sites/conf...building.shtml
Electric Railway Chambers (1912) 11 stories
Source: Manitoba Historical Society
http://www.mhs.mb.ca/docs/sites/elec...chambers.shtml
National Bank Building (1913) 12 stories
Source: Manitoba Historical Society,
http://www.mhs.mb.ca/docs/sites/unio...building.shtml
Hotel Fort Garry (1913) 14 stories
Source: Manitoba Historical Society,
http://www.mhs.mb.ca/docs/sites/fortgarryhotel.shtml
Watkings Building (1914) 9 stories on underpass side
Source: Manitoba Historical Society,
http://www.mhs.mb.ca/docs/sites/watkinsbuilding.shtml
Marlborough Hotel (first three stories in 1914, six story addition in 1923) 9 stories
Source: Manitoba Historical Society,
http://www.mhs.mb.ca/docs/sites/marlboroughhotel.shtml
Paris Building (first five stories in 1915, six story addition in 1917) 11 stories
Source: Manitoba Historical Society,
http://www.mhs.mb.ca/docs/sites/parisbuilding.shtml
Eaton's Mail Order Buildings (1916 and 1921) 9 stories
Source: Winnipeg Downtown Places,
http://winnipegdowntownplaces.blogsp...ail-order.html
Bank of Hamilton Building (1918) 10 stories
Source: Manitoba Historical Society,
http://www.mhs.mb.ca/docs/sites/bankofhamilton.shtml
Federal Building (1936) 11 stories
Source: Manitoba Historical Society,
http://www.mhs.mb.ca/docs/sites/norwester.shtml