Wylie also competed in pairs with partner Dana Graham. Under the tutelage of John Nicks, they won the U.S. junior pairs title in 1980.
Wylie placed second at the U.S. Figure Skating Championships in 1988, 1990 and 1992. His crowning achievement was winning the silver medal at the 1992 Winter Olympics in Albertville, France. After the Olympics, Wylie turned pro.
Wylie attended Harvard University beginning in 1986 and graduated in 1991. He was inducted into the U.S. Figure Skating Hall of Fame in 2008.
Wylie was coached at various points in his career by Evy and Mary Scotvold as well as Carlo Fassi.