Superman #89 (1994)

The Evening Compass (a competitor to The Daily Planet) publishes an article naming Clark Kent as a descendant of the cruelest pirate in history - Captain Kent the Terrible. Perry White challenges Clark to dig into his family records to solve the mysterious disappearance of Captain Kent, when his crewless vessel drifted from a Spanish port in 1588. Superman whirls back in time to 16th century England to witness highwaymen attacking a Royal coach carrying an important person from Queen Elizabeth's castle. Superman disarms and chases off the Highwaymen and is told that the Sea-Side Inn (where Captain Kent stays) is two miles back on the road. When he reaches the Sea-Side Inn no one has heard of Captain Kent, but the important person (the Queen's Ambassador) from the Royal Coach returns to inform him that he, Superman, is Captain Kent and that he must go to the Queen's castle. At the Castle Queen Elizabeth explains that the Spanish King believes that only the cruelest pirate can lead his Armada against England and she demands Superman mislead the Spanish King, by leading his Armada as Captain Kent. Superman agrees (only to avert a war) with the proviso that he will only pretend to be cruel. Queen Elizabeth gives him a letter to be used afterwards to clear his name. Superman is made Captain of a vessel secretly furnished by the Queen, but he has suspicions about some of his rascally crew. His ship attacks an English merchantman, but Superman slaps down the cannonballs at superspeed to prevent ship from being harmed. Superman explains to the crew of the Merchantman that he means them no harm and hides them on an isolated island. He makes up dummies in their place and forces them to walk the plank to impress his pirate crew.

While his ship is docked in Madagascar Superman flies to North America to carve a duplicate of the English settlement of Newtown out of the face of cliffs. One week later, with the Spanish watching, Superman leads his crew in the destruction of the fake settlement. The Spanish leader Don Fernando offers Captain Kent a Dukedom if he agrees to lead the Spanish Armada against England, and Superman accepts the offer.

In Spain Superman becomes suspicious because the plans to launch the Armada are delayed. He captures a spy, who turns out to be his crewman he has been suspicious of, who turns out to be one of the Highwaymen who were attacking Queen Elizabeth's Ambassador. The spy reveals that the Armada sailed two days earlier, so Superman flies back to his pirate ship. He splits the ship into quarters, sets up the pieces in a cloud bank to convince the Spanish that the English are about to surprise them. The ruse works and the Spanish chase the ships into the English Channel where they are defeated by the English fleet led by Sir Walter Drake.