It was not until February 1999 that Debra had her first feud with a female,
Ivory, in the WWF. The feud began with small catfights, but it escalated to wrestling matches. The first match that Debra was involved in saw her team with Jarrett against Ivory and
D'Lo Brown on
Monday Night RAW. Ivory and Brown won by disqualification after Debra hit Ivory over the head with a guitar. They also fought in a tag match at
WWF St. Valentine's Day Massacre where Jarrett and Owen Hart retained their tag titles against Brown and
Mark Henry, who were accompanied by Ivory. On
March 1 1999, Ivory stripped Debra during Jarrett's match. Debra then challenged Ivory to a match backstage, and Ivory accepted. On one occasion, Debra beat Ivory due to the interference from PMS (
Terri & Jacqueline). During the month of April, Debra continued to manage Jeff Jarrett and Owen Hart.
On
May 10, Debra "won" the
Women's Championship from
Sable in an
Evening Gown Match. Technically, in an Evening Gown Match, the winner is the woman who forcibly removes her opponent's dress. Because Sable removed Debra's dress, she therefore should have been the winner. However, Commissioner
Shawn Michaels ruled that he considered the woman who had
lost her dress the winner, crowning Debra the new Women's Champion. During her reign, she rarely defended the title, instead remaining a manager.
Jarrett and Debra then began feuding with
Val Venis and
Nicole Bass, culminating in a match at
Over The Edge 1999 on
May 23. The match that took place immediately after Owen Hart died after falling from the top of the arena while preparing for a stunt. The feud ended in a
bikini contest between Debra and Bass, which Debra won.
Debra lost the Women's Title to
Ivory on
June 14, due to the interference from Nicole Bass. Debra was choking Ivory with a scarf when Nicole entered the ring and choked Debra so Ivory got the pin. Subsequently, she continued as Jarrett's manager. Jarrett began mistreating her during July and August, complaining that every match he lost was her fault. Jarrett then began another feud with D'Lo Brown. The two met at
SummerSlam 1999, with Debra in Brown's corner. However, Brown's former tag team partner Mark Henry turned on him, along with Debra, resulting in Jarrett winning both the
WWF European Championship and the
WWF Intercontinental Championship. The following night, Jarrett awarded Henry the European title and gave Debra an assistant,
Miss Kitty. However, he soon turned against Debra in favor of Kitty, after blaming her for a mixed tag team loss to
Stephanie McMahon and
Test. After losing that match, Jarrett applied the
Figure Four Leglock on her. Finally, at
Unforgiven on
September 26, Debra turned on Jeff Jarrett, becoming a
face, in the middle of his match against
Chyna for the Intercontinental Championship. She smashed Jarrett's guitar over his head and told him she was no longer going to manage him. Chyna pinned Jarrett, but the referee overturned the decision due to Debra's involvement.
The next night on
RAW, Jarrett and
Tom Prichard challenged Chyna and Debra to a mixed tag match. Chyna accepted but added the stipulation that if she won, she would get a re-match for the Intercontinental Championship. Just as Chyna was about to lose, Debra got into the ring and pulled Jarrett's hair, and then Miss Kitty entered the ring to confront Debra. Debra also took her down by her hair. Chyna later pinned Jarrett, so Chyna and Debra won the match. Chyna was rewarded a re-match at
No Mercy. In the following weeks, Chyna and Debra continued to feud with Jeff Jarrett and Miss Kitty.
Debra appeared sporadically thereafter, participating in an 8 women Sudden Death Match for the Women's Championship at
Survivor Series. When Terri got into the ring to break up the pin, Debra got in and stripped
Terri. At the end of 1999 Debra got an offer from
Playboy to appear nude in the magazine yet she turned down the offer.