This is probably not the correct forum, but any input would be appreciated. This is a cribbage board - the best I can come up with it that the aircraft seems to be a combination of a Capelis XC-12 at the front and something like a DH Albatross at the tail. The plane is flanked by what looks like the Union Jack and the former Canadian Flag, with a Maple Leaf. The whole image seems to imply an aviation liaison between the two countries, maybe wartime?