Craybas has won one WTA title at the Tokyo Japan Open. She beat Silvija Talaja in the final after trailing 0–4 in the third set. In the 2006 season, Craybas had reached one quarterfinal at Hobart as the eighth seed, losing to unseeded Italian Mara Santangelo in three sets. She has also reached the semi-finals of a Tier III event in Memphis, a fourth-round showing at the Tier I event in Miami and a further quarter-final appearance at Stanford in late July.
On March 25, 2006, Craybas once again served up an early round defeat of a top seeded player. This time it was No. 2 seed Kim Clijsters in the 2nd round of the NASDAQ-100 tournament. After having lead in both the 1st and 3rd sets, Clijsters eventually lost by a score of 5–7, 6–3, 5–7. It was Clijsters earliest ever exit from the NASDAQ-100, and Clijsters was the defending champion.
Craybas, who may be a veteran on the tour nowadays, is thought to be playing the best tennis of her life. However, after having a successful start to 2006, has fallen short of what was expected of her from her dramatically impressive start, losing to lower-ranked opponents in first rounds or having difficult first round draws against the top players in the world.
She began her 2007 by reaching the semi-finals of a Tier IV event in Auckland, New Zealand. She beat all of her opponents in straight sets before bowing out to Russian Vera Zvonareva 3–6 5–7. She next took part in the Tier II event in Sydney, where she lost in the last round of qualifying to Russian Vera Dushevina in three sets, 1–6 6–3 1–6. At the first grand slam of the year at the Australian Open, she suffered a first-round loss to the number 10 seeded Nicole Vaidisova in three sets, 4–6 7–5 1–6. Jill bounced back into winning form at her next tournament in the USA, at an ITF tournament in Midland. As the number one seed, she beat all of her opponents in straight sets until a hard-fought 2–6 6–3 6–3 victory over the number two seed and fellow American Laura Granville. Due to her lower ranking she has suffered in tough draws, not going further than the second round of any tournament since.
At the start of 2008, Jill Craybas entered the Pattaya Women's Open in Pattaya, Thailand, where, as the 7th seed, she played some of the best tennis of her career and beat Olga Savchuk 6–1, 6–1 in the first round, Renata Voracova 2–6, 6–1, 6–3 in the second round and Andreja Klepac 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 Radwanska in a tie-break in the third set, 2–6, 6–1, 6–7. Craybas's ranking improved from 77 to 60 due to her results.
Jill Craybas was won the Istanbul Cup in doubles.
Jill will represent the United States at the 2008 Summer Olympics in the tennis singles event. She became the last qualifier for the event, replacing Tamira Paszek of Austria. The opening came available when fellow American Ashley Harkleroad elected to skip the games.
|Grand Slam (0)|
|Tier I (0)|
|Tier II (0)|
|Tier III (1)|
|Tier IV & V (0)|
|ITF Tour (4)|
|No.||Date||Tournament||Surface||Opponent in the final||Score|
|1.||March 15, 1998||Nuevo Lareda||Hard||Marina Petrovic||6–2 6–2|
|2.||February 11, 2001||Rockford||Hard (I)||Adriana Serra Zanetti||6-4 6-3|
|3.||October 6, 2002||Tokyo||Hard||Silvija Talaja||2-6 6-4 6-4|
|4.||February 15, 2004||Midland||Hard (I)||Nicole Vaidisova||6-2 6-4|
|5.||February 11, 2007||Midland||Hard (I)||Laura Granville||2-6 6-3 6-3|