Woolsey was coached at Desert Devils in Tempe, Arizona. At the US National Championships in 1989, she took third place in the all-around competition. Later that year she was a member of the US team that competed at the 1989 World Artistic Gymnastics Championships in Stuttgart, Germany. In the team final, where the US took fourth place, Woolsey was the highest-scoring US gymnast. In the all-around competition, she came in eighth. She also qualified to the uneven bars final, where she placed seventh.