I've been compiling a list of all early skyscrapers in Canada built during the "First Great Age" (i.e. those built from 1900-1918) although I'm sure I've missed some. The list includes all buildings over 37 metres, but does not include government buildings like City Halls and Legislatures, factory and warehouse buildings, grand railway hotels or religious buildings.
Montreal
http://wikimapia.org/7655570/fr/%C3%...minion-Express
Edifice Dominion Express (1912) 49 m
https://imtl.org/montreal/building/N...-Insurance.php
New York Life Insurance Building (1888 - considered by some to be Canada's first skyscraper) 46 m
https://imtl.org/montreal/building/E...que-Scotia.php
Eastern Townships Bank Building (1909) 45 m
https://www.spacelist.ca/listings/17...avenue_viger_o
425 Viger Ouest (1910) 45 m
https://imtl.org/montreal/building/E...nt-jacques.php
Hotel Le Saint James/Merchant's Bank (1875, additional floors in 1899/1900) 44 m
http://www.patrimoine-culturel.gouv....n#.XZTJ_0ZKjIU
Edifice McGill (1912) 43 m
https://imtl.org/edifices/Southam.php
Edifice Southam (1910) 42 m
https://imtl.org/montreal/building/E...reign_Bank.php
Edifice Sovereign Bank (1905) 41 m
https://imtl.org/montreal/building/E...an-Express.php
Edifice Canadian Express (1906) 41 m
https://imtl.org/montreal/building/E...haughnessy.php
Edifice Shaughnessy (1912) 41 m
https://imtl.org/montreal/building/E...Sauvegarde.php
Edifice La Sauvegarde (1914) 40 m
https://www.imtl.org/montreal/buildi...s-Building.php
New Birks Building (1910) 39 m
https://imtl.org/montreal/building/Edifice-Duluth.php
Edifice Duluth (1912) 39 m
https://imtl.org/montreal/building/Edifice-Unity.php
Edifice Unity (1912) 39 m
https://imtl.org/montreal/building/Edifice-Lewis.php
Edifice Lewis (1913) 39 m
https://imtl.org/montreal/image.php?id=4774
Edifice Drummond (1915) 39 m
https://imtl.org/montreal/building/E...Versailles.php
Edifice Versailles (1916) 39 m
Toronto
https://www.flickr.com/photos/57156785@N02/7609064352
Royal Bank Building (1915) 90 m
https://www.flickr.com/photos/57156785@N02/11108930955
Canadian Pacific Building (1913) 85 m
https://www.blogto.com/city/2016/11/...er_in_toronto/
Trader's Bank Building (1906) 60 m
http://www.urbandb.com/canada/ontari...l#.XZTm_EZKjIU
302 Bay Street (1917) 56 m
http://www.urbandb.com/canada/ontari.../#.XZToGEZKjIU
Dynamic Building (1910) 41 m
https://en.wikipedia.org/wiki/Temple_Building_(Toronto)
Temple Building (1896, demolished 1970) 37 m
Vancouver
en.wikipedia.org/wiki/Sun_Tower
Sun Tower (1912) 82 m
https://equitablerealestate.ca/vancouver-block/
Vancouver Block (1912) 65 m
https://www.emporis.com/buildings/11...ncouver-canada
Standard Building (1912) 52 m
http://www.vancouversun.com/news/van...250/story.html
Birks Building (1913, demolished 1974) 48 m
http://blog.gryphonliving.com/2018/0...nion-building/
Dominion Building (1910) 45 m
https://pci-group.com/PCIprojects/credit-foncier/
Credit Foncier Building (1913) 41 m
https://equitablerealestate.ca/rogers-building/
Rogers Building (1911) 39 m
https://www.vancouverheritagefoundat...-vancouver-bc/
London Building (1912) 39 m
https://vancouver.skyrisecities.com/...carved-granite
Seymour Building (1920, construction started in 1912 but was delayed due to WW1) 39 m
https://www.vancouverheritagefoundat...-vancouver-bc/
Holden (Tellier) Building (1911) 37 m
Winnipeg
http://archiseek.com/2010/1912-union...ipeg-manitoba/
National Bank (Union Trust) Building (1913) 50 m
http://www.virtual.heritagewinnipeg....eNum=%2004-010
Childs (McArthur) Building (1909, demolished 1988) 49 m
http://www.mhs.mb.ca/docs/sites/unionbankbuilding.shtml
Union Bank (Royal) Tower (1904) 46 m
https://www.flickr.com/photos/bryanscott/2616437973/
Electric Railway Chambers (1912) 45 m
http://www.mhs.mb.ca/docs/sites/bankofhamilton.shtml
Bank of Hamilton (1918) 44 m
https://www.flickr.com/photos/morrismulvey/8715600005
Confederation Life Building (1912) 44 m
https://mccor.ca/portfolio/office-bu...uilding-paris/
Paris Building (1917) 42 m
https://www.pinterest.ca/pin/532761830891866342/
Grain Exchange Building (1908) 42 m
http://winnipeglovehate.com/2008/07/...ay-building-2/
Lindsay Building (1911) 39 m
Other Cities
https://www.cbc.ca/news/canada/calga...ders-1.3581079
Southam Building,
Calgary (1913, demolished 1972) 40 m
https://www.thespec.com/living-story...nnaught-hotel/
Royal Connaught Hotel,
Hamilton (1916) 42 m
https://www.british-immigrants-in-mo..._hamilton.html
Bank of Hamilton,
Hamilton (1905, demolished) 40 m
https://en.wikipedia.org/wiki/File:A...lding_1913.jpg
McCallum Hill Building,
Regina (1913, demolished 1982) 37 m