In 1996 she took part in the US Open with a wildcard . In 1998 she played her first WTA tournament. In the same year she won her first ITF title in Nuevo Lareda. In April 2001 she made her way to the top 100 in the world and took part in all Grand Slam tournaments . In 2002 she reached the second round of the Australian Open after her opponent Mary Pierce had to give up in round one. In September she won her first title on the WTA Tour in Tokyo , although she was 4-0 down in the third set of the final against Silvija Talaja .
In 2004, Craybas reached the quarter-finals in Miami , the largest event after the Grand Slam tournaments. At Wimbledon in 2005 she defeated Serena Williams 6: 3, 7: 6 and reached the quarterfinals for the first time. The following year she beat Kim Clijsters in Miami and achieved her best ranking in singles in 39th place. In 2008 she reached the final in Pattaya , which she lost despite a match ball against Agnieszka Radwańska .
On August 24, 2013, Jill Craybas announced her retirement from professional tennis during the US Open . She played her last match on August 30th in the doubles competition at Flushing Meadows .