In the 1999-00 season, Boca became champion of America once again after beating Palmeiras on the penalti-shootout. Riquelme had an excellent performance during the competition, highlighting his match against rivals River Plate for the second leg of the quarterfinals, where he scored a goal, assisted in another, and made a historic play where he nutmegged from his behind to the River defender Mario Yepes. Boca's successes would continue in the 2000-01 season, winning the Apertura 2000. However, the highest point would be the final of the Intercontinental Cup against Real Madrid, who at that time was in the process of forming "Los Galácticos", with the signing of the Ballon d'Or Luis Figo. Against all odds, Boca ended up winning the match, and Riquelme would be one of the stars assisting for Martín Palermo's second goal with a 30-meter ball, and controlling the pace of play in the last minutes, to which Madrid's defenders Claude Makélélé and Geremi couldn't hold back. During 2001, Boca would not obtain any local title, but would win again in the Copa Libertadores, defeating Mexican Cruz Azul in the finals again through penalties. This time Román would have an outstanding performance against Palmeiras in the semifinal series, where the Argentine midfielder managed to give an assist in the first leg and score a goal in the second leg. Riquelme would be chosen the MVP of the tournament, and would also win the South American Footballer of the Year award for the first time in his career. As the champions of Copa Libertadores his side faced 2001 UEFA Champions League winners Bayern Munich in the Intercontinental Cup final which ended in a 0–1 defeat for his club.