The two reality stars were last-minute additions to the ABC dance-off, replacing injured contestants Jewel and Nancy O'Dell on Monday's season premiere.
Madison, a star of "The Girls Next Door" and four-time Playboy cover model, replaced Jewel, who suffered fractures in both legs during pre-show training. Madison spent five days rehearsing with the singer's professional partner, Dmitry Chaplin.
The pair earned 18 out of 30 points from the judges for their cha cha. Judge Carrie Ann Inaba told Madison not to be discouraged, but described her as "kind of like a newborn deer right now with wobbly legs."
Madison said her first dance performance was "really scary."
"I definitely could have used the extra time," she said, adding, "I don't really have any dance experience."
That wasn't the case for Rycroft, began rehearsing Saturday. Though Tom Bergeron noted that she was "the performer with the least amount of training in the history of the show," Rycroft's past dance experience helped her and professional partner Tony Dovolani earn 23 points for their waltz.
A former Dallas Cowboys cheerleader, Rycroft said she also has a background in ballet.
"The two days we put in, it feels like it paid off," she said after her performance.
The judges seemed to agree. Bruno Tonioli called her "a revelation."
"I don't know that Bachelor guy, but he's a loser," he said.
Jason Mesnick proposed to Rycroft on ABC's "The Bachelor" last week, but changed his mind on the show's season finale. She was tapped to fill in for O'Dell on Friday.
O'Dell and Jewel both sat in the audience for the show's season eight premiere. O'Dell, who tore soft tissue in her knee during pre-show practices, wore a knee brace and said she will have surgery soon, followed by six to eight weeks of rehabilitation. Still, she rose to her feet and gave a thumbs-up after Rycroft's performance.
Jewel, who said, "My will to dance was stronger than my bones," will return to the ballroom next week to sing on the first results show. Her husband, rodeo champ Ty Murray, remains a contestant.
Other competitors include Apple co-founder Steve Wozniak, rapper Lil Kim, former football star Lawrence Taylor, Olympic gymnast Shawn Johnson, singers Chuck Wicks and Belinda Carlisle, TV personality Steve-O, and actors David Alan Grier, Gilles Marini and Denise Richards.
Marini was the top dancer Monday, scoring 24 points for his cha cha with partner Cheryl Burke. Wozniak came in last place, earning 13 points for the same dance with partner Karina Smirnoff.
Judge Len Goodman praised the computer guru for having fun with his performance, but said, "overall, it was a disaster."
Added Tonioli: "It was like watching a Teletubby going mad in a gay pride parade."
"That's almost a compliment," Wozniak quipped.