Left one is Model T plug and head, same basic wrench with only minor variations used for all of them. Right one is later...basic style was used from 1928 into early 1940, 11/16 head nut, different spark plug sizes changing in 1933 and 1937. My flying guess from eyeballing plug opening is '33-7, most of those have the part number prefix "40".
40-17????.