1869: A new $5 note was printed with a portrait of Andrew Jackson on the left of the face.
1886: A silver certificate $5 note with a portrait of Ulysses Grant on the right of the face.
1896: A really unusual silver certificate $5 note in that (unlike other series of U.S. currency where the opposite is true) the designs were on the front and the portraits were on the back! The portraits were Ulysses Grant on the left and Phillip Sheridan on the right.
1899: A new silver certificate $5 note with a portrait of Running Antelope on the face.
An 1896 $5 Silver Note
Federal Reserve history
1914: Began as a large-sized note with a portrait of Abraham Lincoln on the face