I believe the chip inlay and the pinback picture are the same. Not similar but the same

Both the pinback and chip inlay are made of a litho on paper covered with clear celluloid. The two lithos are the same size

If the lithos were made while the jockeys were active, the chip and pinback could well be pre 1900. Of course both items could have been made after their careers ended.

The only thing I pretty sure of is that both are pre 1911 (the earliest date I have of a USPC c&s)

I have pinbacks for 5 or 6 American jockeys as well as a similar number of English jockeys. I think there are several more jockey chips out there.