Madusa soon aligned herself with Evan Karagias after he came to her aid after she lost to Meng in a match on Nitro in October 1999. The two developed a romantic bond the very next week on Nitro as they let their affections for each other be known in an unusual match. During the match, the two didn't exactly grapple, but rather, they exchanged romantic pleasantries throughout the contest. For starters, Madusa felt up his chest, pinched his backside and batted his baseball cap off in a playful manner. Evan returned the favor by grappling her into some promiscuous wrestling positions and whispering sweet nothings into her ear - to her liking no less. At one point, a smirking Madusa backed him into a corner and attempted to seduce him by shoving her massive breasts in his direction. The match came to conclusion when she smothered him with a large kiss as she pinned him for a victory. Karagias didn't mind losing the match and he made her his manager. Madusa would help lead him to the WCW Cruiserweight Championship at WCW Mayhem 1999. Soon after his title win, Madusa became interested in Evan's Cruiserweight Championship belt.
Madusa earned a title shot at WCW StarrCade on Monday Nitro when she defeated Mona and Evan Karagias in a three-way match. Then at StarrCade, Madusa defeated Evan to become the first female to win the WCW Cruiserweight Title. Madusa had dumped Evan a week before the bout when she caught him flirting with Spice backstage. Spice became Evan's new girl and she was in his corner at StarrCade; however, Spice distracted Evan during his match with Madusa at StarrCade to help Madusa reign victorious. Spice them aligned herself with Madusa and she became her manager. The relationship only lasted about a month as Spice returned to her role as a Nitro Girl soon after.
Though her reign as WCW Cruiserweight champion was short-lived, a few memorable moments took place nonetheless. On the January 10, 2000 edition of Nitro, Madusa inexplicably came out wearing a blue wig,and an ill-fitting bikini top, that had a difficult time containing her immense, pendulous breasts. Madusa's bizarre look was akin to a female Anime character come to life in that female Anime characters have colorful hair, curvaceous physiques and wear gaudy outfits. On this edition of Nitro, Madusa came out to tend to Asya after she was struck by Oklahoma with a bottle of barbecue sauce during a match. Oklahoma then struck Madusa from behind with a broom. And thus her feud with Oklahoma started.
Perhaps the most memorable moment of her reign as Cruiserweight champ took place in an evening gown match with Oklahoma on an episode of WCW Thunder on January 12, 2000. Madusa easily defeated Oklahoma by stripping off his dress. After the match, Oklahoma retaliated and struck Madusa with a glass bottle containing barbecue sauce. Oklahoma then disrobed Madusa to reveal her blue undergarments. With her mammoth breasts billowing out of a push-up bra, Oklahoma proceeded to pour the BBQ sauce down her mountainous cleavage. Oklahoma then kicked Madusa in the back and she fell to the floor outside the ring. She eventually lost the belt to Oklahoma at WCW Souled Out in January 16, 2000. During her reign, Madusa would only defend the WCW Cruiserweight Title on television on two other occasions. She defeated Asya on the first edition of WCW Thunder of 2000. She also defeated a male plant on the January 15, 2000 edition of WCW Saturday Night. Madusa would also defeat Sherri Martel in a non-title match on Thunder.