He also made his first class debut for their senior side, the Free State Cheetahs during the 2009 Currie Cup Premier Division, coming on as a late replacement in their match against the Sharks, but finishing on the wrong end of a 24–13 result.
[3] He was heavily involved in theFree State Cheetahs' 2010 Vodacom Cup campaign, starting eight of their ten matches in the competition to help them reach the final for the third time in their history.
Nevertheless, he still played a crucial part in their season, scoring a total of 56 points – second only to Strydom for the Kings[10] – to help them finish in second spot in the log.
[17] The Kings signed Demetri Catrakilis to be their first-choice fly-half and kicker, which meant that Whitehead was mainly used as backup to him and fullback SP Marais.
He was an unused substitute in the Kings' historic first-ever Super Rugby match, which they won 22–10 against Australian side the Force,[18] but made his debut the following week as he came on as a late replacement in their 12–21 loss to the Sharks.
[19] After another appearance off the bench against the Chiefs,[20] Whitehead made his starting debut in their 20–55 loss to the Crusaders in Christchurch and marked the occasion by scoring his first Super Rugby try, which he also subsequently converted.
[21] He also started in their loss to the Hurricanes,[22] as well as their match against the Brumbies in Canberra, where an injury-time Cornell du Preez try and subsequent conversion from Demetri Catrakilis earned the Kings a 28–all draw to secure their first log points outside of South Africa.
[26][27] Whitehead appeared nine times for the Eastern Province Kings in the 2013 Currie Cup First Division season, scoring two tries and kicking five conversions and they once again qualified for the final.
He made just one appearance in the 2014 Vodacom Cup, scoring the EP Kings' only points in a 3–31 defeat to Free State XV in Cradock.