The 1999 Skate America was the first event of six in the 1999–2000 ISU Grand Prix of Figure Skating, a senior-level international invitational competition series. It was held at the World Arena in Colorado Springs, Colorado on October 27–31. Medals were awarded in the disciplines of men's singles, ladies' singles, pair skating, and ice dancing. Skaters earned points toward qualifying for the 1999–2000 Grand Prix Final. The compulsory dance was the Viennese Waltz.