A Lego Senior Yo-Yo 99 circular brass pin, circa mid to late 1930s.
Because Cheerio sold their "99" model in Great Britain -- and likely other parts of Europe -- it is easy to mistake this pin as a Cheerio "99" award pin. However, the pin was made in Stockholm, Sweden. See the image in this exhibit Pin, back, large. That piece of information is important to its identification. Lego of Denmark, founded in August 1932, began by initially creating and selling small wooden toys. Two of those toys that they made were the "Yo-Yo 99 Junior" and the "Yo-Yo 99 Senior" (see image Lego 99 Junior and Senior models). Aside from the color and imprint on each yo-yo's face, the differences between the Junior and Senior models are very subtle. Both have the same profile and the same outer diameter. However, the Junior model has a slightly larger diameter flat face compared to the Senior version.
The pin in this exhibit is associated with Lego's Senior 99 model. What is unknown is whether a player had to successfully perform a series of tricks to earn this Senior pin or whether it was simply given to a player by a demonstrator or someone else. It was most likely the former. The Senior 99 pin suggests that there was also a Lego Junior Yo-Yo 99 pin.