In 1996, Kathy found regular work on Canadian television on the family drama series Wind at My Back, where she spent five years, full-time, playing Grace Bailey, a junior radio M.C. in the small town of New Bedford in Ontario during the Great Depression; Kathy's portrayal of Grace Bailey was nominated for a Gemini Award for Best Performance By an Actress in a Continuing Leading Role. In 1999, Kathy was cast as Denise Stanton in the TV movie Switching Goals, starring Mary-Kate and Ashley Olsen. Later that same year, Greenwood crossed the border and commuted to Los Angeles to appear on such shows as The Drew Carey Show, the update version of Hollywood Squares, and the American version of the improvization game show Whose Line Is It Anyway?.