After understudying in several productions at the Springfield Theatre Centre, Aylesworth was cast in the role of Consuelo in West Side Story, while her family was preparing to move to Seattle, Washington.
[7] Aylesworth's performance in Peter Pan brought her to the attention of talent scouts at ABC, leading to the beginning of her television and film career as Rebecca Lewis on the soap opera One Life to Live.
[8] After her character was written out of One Life to Live, she appeared in the independent film Childhood's End and the final episode of the HBO series Lifestories: Families in Crisis.
Aylesworth continued her work on television with guest appearances in The West Wing, Law & Order: Special Victims Unit, and Ed[9] as well as being cast in a lead role in the supernatural hospital drama All Souls.
[15] Upon being released from 24, Aylesworth was cast as Chandra Moore, a DNA analyst, in the fifth season of CSI: Crime Scene Investigation; while the role was intended to be recurring, it was dropped after one episode.
[18] Following her departure from 24, Aylesworth landed her first leading role in a feature film – the independent, romantic drama Crazy love where she worked alongside Bruno Campos and former 24 costar Paul Schulze.
Crazylove tells the story of Letty Mayer, a school teacher who suffers a nervous breakdown and while institutionalized, meets Michael (Campos) and the two begin a dangerous and unpredictable romance.
Aylesworth's character, Angelina Marveau, was "a fallen French nun" who was fighting to choose between her religious beliefs and first love, a nihilistic, American professor, who was portrayed by Woodside.
In the Kevin Costner movie, Mr. Brooks, Aylesworth portrayed a divorce lawyer, Sheila, who was representing the husband of Demi Moore's character, Detective Tracy Atwood.
Departing from her previous type of characters, Aylesworth played the femme fatale Audrey Levine in the Gideon Raff independent thriller The Killing Floor.
[25] Her character, Kelly O'Brien, an Army pilot and soldier returning home after being deployed overseas, arrives in Gunnison, Colorado the day before the Aliens and Predator invade the town.
In January 2007, Aylesworth had a guest role in two episodes of the ABC comedy, The Knights of Prosperity, where she played the head of Mick Jagger's security company, Simone Cashwell.