Early in his career, Wakefield played predominantly on the second tier Challenge Tour before winning a place on the European Tour via qualifying school at the end of 1999. He failed to retain his tour card during his rookie season and dropped back to the Challenge Tour for 2001. He won his first professional tournament in 2002 at the Tessali Open del Sud, and went on to finish 9th on the Challenge Tour Rankings to graduate back to the European Tour for 2003.
Wakefield finished the 2003 European Tour season inside the top 100 on the Order of Merit to retain his card, but was back at the tour school at the end of 2004 having just missed out on keeping his place via the money list. He won his card back, and has secured his place on the European Tour since then with solid performances, although he has yet to win a tournament at the highest level. In 2005, he won his second professional title, the Dimension Data Pro-Am in South Africa.