Aside from attending McDonald College he attended an acting course at the Zenith Theatre in 2003. Wakefield finished Year 12 at McDonald College of Performing Arts in 2006.
His first professional acting role was an uncredited appearance in the film Bootmen in 2000. This was later followed by a television appearance playing Brad, a guest star in the 2001 series Don't Blame Me for which he appeared in two episodes, Best Foot Forward and The Dingo Made Me Do It. Wakefield played his first leading role in a feature film in The Black Balloon as Thomas Mollison. The film opened on 6 March 2008 in Australia. The film's world premiere was at the Berlin International Film Festival in Germany in February 2008, where the film received a Crystal Bear as the best feature-length film in the Generation 14plus category.
In August 2005, Wakefield secured his first regular TV role playing Lucas Holden in the long running Australian Soap opera Home and Away. His character was the youngest child of the Holden family until his dad Tony and stepmother Rachel had his baby brother Harry. His performance in series led to a Logie Nomination for the Best New Talent in 2006. During his time on the show he was involved in a controversial storyline which led the Australian broadcasting regulator (ACMA) to conclude that scenes had breached the Australian broadcasting code, a finding which was responsible for the series being re-classified as PG.