Hmm. To be honest, there’s essentially nothing on the Digit Shield that can fail. It’s so simple. If the two right digits are working then that means both chips are working. The only distinction between left and right displays is the transistors. The two left-most transistors on the board are associated with the left display. Maybe double check the connections there.
Or load a different program on the Arduino that just displays numbers on the left and see if it works?
Mike