History Mystery

Many years ago, while cleaning our storage room, my wife pulled this out of a box and said, ‘Do you want this?’
I had never seen it before and took only a split second to answer, ‘Yes!!’
The larger trophy is a ‘perpetual’ from the Ottawa Fair, first presented in 1908. The smaller is the ‘keeper’…we will ignore it. The trophy is Edwardian in style, and is ‘quadruple silver’ plated. When it came out of the box it was black and in very poor shape. I am led to believe it sat at the entrance of a house and pockets were emptied of keys and change into it. The inside of the bowl is worn of most of its silver. The top rim has a serious bent, seen here on the left. The bowl and its rim are supposed to be level. Someone has perhaps sat on it, and now it tilts to the rear, or right in the photo.
I liked that it old and interesting, but on closer examination, I saw that it would be useful for posing a mystery to my Canadian History class. See if you can solve the mystery better than they did.
Look at the first extra photo and state, in plain language, what the trophy was presented for. (Easy…but no one ever solved this)
Look at the second extra and explain why Robert Crouch was the last winner (and eventual owner) of the trophy in 1912-13.
Answers tomorrow.