Caligiuri is probably best remembered for the "Goal Heard Round the World," which he scored in a World Cup Qualifier November 19, 1989 against Trinidad & Tobago, which qualified the United States for the 1990 World Cup in Italy, the first World Cup the United States had played in since 1950. Caligiuri was, however, far more than that single goal - he had a distinguished career, both for club teams and for the United States national team. On top of that, Caligiuri would go on to score the first World Cup goal for the national team in 40 years, scoring in a 5-1 defeat against Czechoslovakia.

Caligiuri attended UCLA from 1982 to 1985, was named an NCAA All-American twice, was named 1986 U.S. Soccer Athlete of the Year, and captained the Bruins to an NCAA Championship his junior year. While at UCLA Caligiuri also earned his first cap for the national team, playing October 9, 1984 against El Salvador. Caligiuri would eventually tally 110 appearances for the United States, and would add five goals from his position in the midfield. Caligiuri was a central figure to the national team throughout the 80's up to the mid-90's, and would start every match in both the 1990 and 1994 World Cups, playing his final game in 1997, thirteen years after his debut.

Caligiuri finished his MLS career with 9 goals and 14 assists, accumulated over 135 games, 123 of which were starts.

In 2004, Caligiuri was elected into the United States National Soccer Hall of Fame, along with Michelle Akers and Eric Wynalda. He currently serves as an athlete representative on the Board of Directors of the United States Soccer Federation.

He coached the Cal Poly Pomona men's soccer team through 2008.