Whitehead has competed in numerous competitions throughout his career, starting in 2008.
In 2009, he won the 2009 Kent Open, beating Steve Douglas in the final.
He reached the quarter-final of the 2017 BDO World Trophy, his best TV major performance to date.
This was equalled at his third appearance at the BDO World Darts Championship (in 2019) where he knocked out top-seed Mark McGeeney before losing to Scott Waites in the quarter-finals.
In January 2019, Whitehead entered PDC UK Q-School and did enough to earn a two-year tour card by finishing in the top 11 of the Order of Merit.