P.M.S. gained a "Love slave" named Meat in May 1999. In the same month, the stable expanded once more to incorporate Ryan Shamrock, who had been spurned by the womanizing Val Venis. Shamrock left both the stable and the WWF in the following months, while Terri and Jacqueline assisted Meat in his matches. Tension began to grow between the two women as Terri (kayfabe) exhausted Meat with hours of sex before his matches and then berated her fatigued lover when he lacked the energy to win matches. Jacqueline left the stable after Terri forced Meat to kiss her feet on the August 1 episode of Sunday Night HEAT.
On the September 6 episode of RAW, Jacqueline faced the misogynistic Jeff Jarrett in advance of his Intercontinental Championship match with Chyna. Jarrett squashed Jacqueline, choked her with the ring ropes, forced her to submit with the figure four leglock, and broke a guitar over her head.
Jacqueline soon returned to her pursuit of the Women's Wrestling Championship, which she failed to win from Ivory in a three way hardcore match which also included Luna on November 18. On November 25, Jacqueline defeated Ivory in a "gravy bowl match" to win the Golden Ladle Trophy. At Armageddon 1999 on December 12, she took part in a four way evening gown match for the Women's Wrestling Championship but was stripped following a combined assault from her opponents, Ivory, Miss Kitty and B.B..
Jacqueline won the WWF Women's Wrestling Championship for a second time on February 1 by defeating Harvey Wippleman (who had won the belt from Miss Kitty while in drag and calling himself "Hervina") in a very short match. Her reign lasted throughout February and March, with Jacqueline defeating Ivory and Lita to retain the title. On March 28, she was challenged by Stephanie McMahon, and the inexperienced Stephanie defeated Jacqueline following extensive interference from D-Generation X.
Jacqueline's requests for a rematch were denied, and she lost a battle royal for the number one contendership to Lita. On the July 2 episode of Sunday Night HEAT, WWF Light Heavyweight Champion Dean Malenko challenged "anyone with enough manhood" to face him. After Jacqueline came to the ring, Malenko explained that he had said "manhood, not somebody from the hood." Jacqueline was granted a title shot, but submitted to Malenko's Texas cloverleaf.
Throughout August and September, Jacqueline feuded with WWF Women's Wrestling Champion Lita, aligning herself with Edge and Christian to counter the presence of Lita's constant companions, The Hardy Boyz. She received further title shots on October 9 and November 2, but failed to unseat Lita on both occasions.
The Acolyte Protection Agency (Faarooq and Bradshaw) recruited Jacqueline on the December 18 episode of RAW, asking her to take care of Trish Stratus while they fought Stratus' clients, T & A. In the resulting six person tag match, Jacqueline pinned Stratus. On the December 21 episode of SmackDown!, Jacqueline challenged Right to Censor member Ivory to a title match. After the other members of R.T.C. distracted Jacqueline and enabled Ivory to pin her, the A.P.A. repaid the favor by saving Jacqueline from a group beating after the match.
The feud between the A.P.A. and R.T.C. continued throughout early-2001 and culminated in a match at WrestleMania X-Seven on April 1, which pitted R.T.C. (Bull Buchanan, The Goodfather and Val Venis) against The A.P.A. and Tazz. In the early stages of the match, Jacqueline DDT'ed Stevie Richards, the leader of R.T.C. who had accompanied them to ringside. R.T.C. lost the match after Bradshaw pinned The Goodfather.
In mid-2001, Jacqueline, along with Tazz, Al Snow and Tori, became a trainers on the MTV reality TV series Tough Enough.
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