Boitano first made his mark on the international scene when he won the bronze medal at the 1978 World Junior Figure Skating Championships, beating future rival Brian Orser for that medal.  In 1982, Boitano became the first American to land a triple axel. He was known primarily as a jumper early in his career and he, along with several other skaters, helped push the technical envelope of men's skating.

Boitano placed second at the 1984 United States Figure Skating Championships, earning himself a trip to the 1984 Winter Olympics. He placed 5th at the Olympics, setting the stage for his success over the next four years. Boitano won the 1985 United States Figure Skating Championships, the first of his four titles. A few weeks before the 1986 U.S. Championships, he had injured tendons in his right ankle but went on to win his second national title.  Later that year, Boitano took the title at the 1986 World Championships.

In the 1988 United States Figure Skating Championships, Boitano performed a flawless skate.  He won the competition, and went into the Olympics as the U.S. National Champion.  Boitano and Orser were going head to head the entire Olympics and it came down to both of their free skates.  Boitano won the battle and gold medal, wearing skates with American flag embroidery.

Following the Olympics, Boitano went on to dominate competitions in the professional ranks, winning 10 straight professional competitions, including 5 consecutive World Professional Championship titles and 4 consecutive wins at the Challenge of Champions.  He was later inducted into the World Figure Skating Hall of Fame and the United States Figure Skating Hall of Fame in 1996.