1633 saw the Ming dynasty crush the Dutch East indies fleet at the Battle of Liauouo Bay. The Chinese Imperial fleet used iron cannon that they'd bought from England to whip the Dutch who were probably the greatest maritime power of the age. Not that it helped the Middle Kingdom in the long term, although the Manchu dynasty restored Chinese power for another 200 years.
1710 saw the turn of Admiral Cloudesley Shovell, commander of a Royal Navy fleet returning from the Mediterranean to England. A couple days prior a rating had come to his commanders saying that his Dead Reckoning navigation showed the fleet to be seriously off course from where the Fleet navigators thought it was, and was in grave danger of running on unexpected rocks. Shovell had him hanged for insubordination. On October 22 the entire fleet ran aground on the Scilly Isles in the English Channel just as the Rating had warned, in one of the most unfortunate upsets in Royal Navy history. Thousands of sailors were lost, as were many of His Majesty's Ships of the Line. Admiral Shovell drowned with his fleet. The episode caused Parliament to pass the Longitude Act, leading to the invention of the chronometer.
1790 saw the defeat of the U.S. Army by the Miami tribe warriors under chief Little Turtle at what would be Ft. Wayne. The setback was temporary, as Miami University of Ohio leads us to believe.
1844 was supposed to see the end of the world on this day. The next day went down in history as The Great Disappointment.
1895 saw a train unexpectedly beat a buffer stop at the Gare Montparnasse in Paris. The train "won".