By the time she retired in 2013, she was one of the oldest players on the WTA Tour at 39 years of age, as well as the longest serving, having turned pro in 1996.

[1][2] Craybas graduated from the University of Florida with a bachelor's degree in telecommunications in 1996, and has said in interviews that she hopes to enter film or television production when her playing career ends.

[3][4] Craybas credits her achievements to her long-time coach, Raja Chaudhuri who has worked with her from the start of her tennis career.

In the 2006 season, Craybas reached one quarterfinal at Hobart as the eighth seed, losing to unseeded Italian Mara Santangelo in three sets.

At the first Grand Slam tournament of the year at the Australian Open, she suffered a first-round loss to the tenth-seeded Nicole Vaidišová.

As the top-seeded, she beat all of her opponents in straight sets until a hard-fought 2–6, 6–3, 6–3 victory over second-seeded and fellow American Laura Granville.

At the start of 2008, Craybas entered the Pattaya Open, where, as the seventh seed, she played some of the best tennis of her career and beat Olga Savchuk 6–1, 6–1 in the first round, Renata Voráčová 2–6, 6–1, 6–3 in the second, and Andreja Klepač 6–4, 6–4 in the quarterfinals.

In the semifinals, she beat Akgul Amanmuradova 6–4, 6–0, and lost to the top seed Agnieszka Radwańska in a tie-break in the third set.