“During maritime operations of the Weapons Systems Evaluation Program over the Gulf of Mexico, an MQ-9 remotely piloted aircraft fired a Hellfire missile at a sea-going target for the first time. As engineers, pilots and scientists watched on wall-mounted TV screens, the missile hit a boat being towed by another remotely controlled vessel.”

Source: Reaper drone hits sea-going target with Hellfire missile for 1st time in Gulf training – U.S. – Stripes