^ I think you're correct - the Drummond Court building is the one squished on the right.
By my estimate we are looking at Drummond St vaguely towards the north, on the block just south of de Maisonneuve. The part of the Drummond Court where the tunnel was later cut out would be at the far edge of the frame.
The building in the centre of the frame looks to me like it would be the 12-story annex to the old Drummond YMCA, built in 1930 according to this link:
http://archives.concordia.ca/drummond-ymca
(picture in the article is of the main YMCA building dating back to 1912. Looks like both were demolished around the same time in 2002).
This would explain the caption on the photo you posted.
Since we're at it, here is a picture of the constructionof the Peel station on the green line, directly underneath the newly opened de Maisonneuve (taken at Peel / de Maisonneuve looking west, probably circa 1962). The Drummond Court tunnel is clearly visible in the background, and the YMCA annex peeks out the left edge of the frame:
http://emdx.org/rail/metro/Images/ConstructionPeel.jpg