ISS Pro Evolution 2 (known as World Soccer Jikkyou Winning Eleven 2000: U-23 Medal e no Chousen, "World Soccer Live Winning Eleven 2000: Challenge for the Olympic Medal" in Japan) is the fourth video game in the ISS Pro series and the second installment of the ISS Pro Evolution series, developed exclusively for the PlayStation by Konami Computer Entertainment Tokyo, a division of Konami it was available in Europe and Japan but not available in North America due to the previously released enhanced remake version of the previous entry in the series, ISS Pro Evolution, retitled ESPN MLS GameNight with MLS licenses.

The game received highly positive reviews from critics, scoring 95/100 on Metacritic.

[4] Gideon Kibblewhite of GamesRadar+ gave the game Direct Hit citing that "The best football sim in the world just got better.

"[5] However Swedish video game magazine Super PLAY gave the game 7 out of 10 citing that "In summary, it is possible to say that ISS Pro Evolution 2 is another step away from the layout once made International Superstar Soccer so unique.

"[6] According to the Japanese magazine Famitsu ISS Pro Evolution 2 sold a total of 362,989 units in Japan by the end of 2000, making it the 21st best-selling game of the year in the country.