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.

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.

Timothy Goebel made history by becoming the first person to land three quadruple jumps in one program.

In the men's free skating, he landed a quad salchow, a quad toe loop in combination, and a quad toe loop as a solo jump.