Complain Away sent in this picture and declared:

The only way this apostrophe is justified is if this word becomes part of a sentence like “This up-do’s even worse than her botox.”

Scott writes:

I am hoping that this will live up to the claim of “Oldest Cited Example”!

I have attached [a photo] of an old religious poster. Of interest is the text on the lines from Earth at the bottom to Heaven on the right — “40 DAY’S, WAY’S”. (I also like how “God, Jesus, and the Angles” are advertised as living in heaven!)

I found this display at the Virginia Historical Society in Richmond, VA. There is no placard for the poster in question, but in context of the notes around the display, I think it should be dated in the early 1800s.