Askegard was born in Minneapolis, Minnesota, on 6 January 1969 and began his dance training at the age of five with Loyce Houlton and the Minnesota Dance Theatre.
He continued his studies in Minneapolis until the age of 16, spending one summer at the School of American Ballet.
In 1997, he left ABT to join New York City Ballet as a soloist and was promoted to principal the next year.
Askegard appeared in PBS' Live from Lincoln Center broadcast, "New York City Ballet's Diamond Project: Ten Years of New Choreography" in 2002, dancing in Them Twos and two years later in the Live From Lincoln Center broadcast, "Lincoln Center Celebrates Balanchine 100," in Vienna Waltzes.
Askegard danced his farewell performance the last day of the fall 2011 season, Sunday, October 9; the program consisted of the Diamonds pas de deux from Jewels, Episodes, In Memory of ... and Western Symphony.