Deep Blue versus Garry Kasparov
Garry Kasparov, then-world champion in chess, played a pair of six-game matches against Deep Blue, a supercomputer by IBM. Kasparov won the first match, held in Philadelphia in 1996, by 4–2. Deep Blue won a 1997 rematch held in New York City by 3½–2½.
Source: Wikipedia — Deep Blue versus Garry Kasparov (CC BY-SA 4.0)