5.
Captain Erika Hernandez, captain U.S.S. Columbia, NX-02 (various episodes of Enterprise, the
Destiny series of novels)
4.
Captain Data, acting captain U.S.S. Sutherland, NCC-72015, captain U.S.S. Enterprise, NCC-1701-E, captain U.S.S. Enterprise, NCC-1701-F (TNG: "Redemption", the pre-ST:2009 comic series Countdown, TNG novel "Imzadi")
3.
Captain Morgan Bateson, captain U.S.S. Bozeman, NCC-1941, captain U.S.S. Atlas, registry unknown (TNG: "Cause and Effect", Star Trek: First Contact, misc novels)
2.
Captain Spock, captain U.S.S. Enterprise, NCC-1701, captain U.S.S. Surak, registry unknown. (TOS movies, misc novels, DC Comics Star Trek series)
1.
Commodore Sarah Chandler, captain of U.S.S. Triumphant, NCC-170090, and Fleet Commander for the auxiliary ships attached to the farship U.S.S. Aurora (my fan fic captain)