The 1998/99 Cross-Country World Cup began on November 28, 1998 in Muonio and ended on March 20, 1999 in Oslo . The highlight of the season was the 1999 Nordic World Ski Championships from February 19th to 28th in Ramsau . For the individual competitions held there - for the last time for world championships - World Cup points were also awarded, although only the two best placements of an athlete were counted. The sprint competitions held between Christmas and New Year in Garmisch-Partenkirchen , Engelberg and Kitzbühel were only rated for the sprint & middle distance discipline, but not for the overall World Cup. The sprint in Milan, on the other hand, also counted for the overall World Cup.
Victory in the men's overall World Cup ranking went to Bjørn Dæhlie from Norway for the sixth time . Dæhlie is so far the only athlete to have achieved a sixth win. He passed Gunde Svan , who was able to fight for the overall victory five times. During the season, Dæhlie took five wins and four other podiums. In his career he was able to celebrate a total of 46 World Cup victories, making him the most successful athlete to have participated in World Cup competitions (as of November 2009). The second place went to the Austrian Michail Botwinow , who could clearly refer the Finn Mika Myllylä to the third place. Botwinow secured the discipline classification of the long distance competitions ahead of Dæhlie and Myllylä. This makes him the first Austrian athlete to win an overall ranking in the cross-country world cup. The sprint & middle distance classification won - for the first time in his career - Bjørn Dæhlie, who ended his active career after the season. His compatriot Tor Arne Hetland was second in this ranking ahead of Mathias Fredriksson from Sweden .
While the men's season was clearly dominated by Dæhlie, who was the overall winner early on, the women's standings were not decided until the season finale. Before the last competition, the Norwegian Bente Martinsen was clearly ahead of the Italian Stefania Belmondo with 71 points . While Belmondo, who had her strengths in the longer distances, accommodated the length of the final competition of 30 kilometers, sprint specialist Martinsen again revealed her weaknesses in the longer distances. Belmondo finished second in Oslo behind Julija Tschepalowa and was able to secure 80 points. Martinsen, on the other hand, was only able to take 22nd place, which increased her points account by another 9 points. This meant that both women were able to score 768 points in the overall standings and thus, for the first time in the history of the cross-country skiing world cup, victory in the overall standings was decided due to the higher number of wins this season. Since Martinsen won seven competitions during the season, while Belmondo was only successful twice, the big crystal ball went to Martinsen for the first time in her career. Third place went to the Russian Nina Gavriljuk . The victory in the sprint and middle distance classification also went to Martinsen in front of the Czech Kateřina Neumannová and Kristina Šmigun . The Estonian also won the long distance World Cup ahead of Belmondo and the Russian Larissa Lasutina .
Norway won the Nations Cup ahead of Russia and Sweden. While Russia won the women's standings with ease, Norway also won the men's championship.