Just a couple of guesses re the pics(1) in the hockey picture could the fellow on the bottom right be Gerry McKenna and (2) could the Caverley picture have been taken on Churchill opposite Cunningham's store between Devonshire and Murray.
As a sidebar, I remember putting my skates on at home on Murray and skating down the streets to the rink at Empire and Churchill and playing shinney with one puck and maybe 20 players evenly split into two teams.
The wonder of it all was how we remembered who was on each team because there were no uniforms and age was no barrier. I also remember at least three people who managed the rink --Stan Charles Sr, Abbie Philp who also worked at The Country Club of Montreal in the summer and Jess Bowbrick who doubled as a taxi driver for Arrow taxi.
Anyone who was in the Park at the time will also remember the great hockey games on a Fri night(if memory serves me correctly) between The Maroons and The Monarchs. They will also remember that if you stayed playing on the rink until it was time to close, you got dragooned into helping to clean the ice surface,either scraping with a plow,sometimes three abreast, or shoveling the scraped snow over the boards so that the ice could be resurfaced (flooded) for the next day.
As my buddy Swinnie says The picture of the rink brings back great memories.
PS does anyone out there remember that the Gurd's sign above the store in the Caverley Pic was for Gurd's Ginger Ale