Cunningham won the Pardey Shield tennis title at the age of 13, which made her the youngest winner of the prestigious Tasmanian schools competition.

Her best performance on the WTA Tour was a semifinal appearance, partnering Jo-Anne Faull at the Malaysian Women's Open in 1993.

She won two ITF singles titles: at Lee on Solent, and in Ballarat, in 1994[4][5] Cunningham retired from tennis in 1996.

Her roles during her ten year career at the WTA included being the Vice President of Player Relations and On-Site Operations.

Her father ran the local real estate company, Woolcock Partners, for 40 years, before it was bought by her elder brother Sam in 2013.