Before reading this post, check out the related Vintage Toronto Ad on Torontoist.
The ad that Dr. Risk ran in the Toronto Star from May 1899 to January 1900—this sample was taken from the May 20, 1899 edition.
In January 1900, Dr. Risk left the firm (death? buyout? wanderlust?) and Dr. A. Rose took over. From the sound of this ad (taken from the January 20, 1900 edition of the Star) it appears there a few changes were made to the office—maybe Dr. Rose didn't like Dr. Risk's taste in furniture or equipment. Note how Dr. Rose holds the line on teeth prices in the face of the Great Teeth Price Surge of 1900.
From the November 16, 1901 edition of the Star, the latest ad I could find for the office. It had moved north around April 1901 to Yonge and Shuter, roughly where the entrance to the Eaton Centre parking garage is. McKendry's was a clothing store at Yonge and Albert streets that advertised "mourning millinery" among their wares. The lady is still beaming after two years of serving as the office's mascot—how much longer she smiled, I cannot say.