[6] In March, Sherwood was in the United States negotiating a sponsorship deal with Red Bull when a rider withdrew from the X-Fighters series, backed by the drinks company.

[7] At age 17, Sherwood competed in his first professional event and clinically beat the best riders in the world in front of 42,000, winning the opening round of the Red Bull X-Fighters in Mexico.

Despite not being able to repeat his debut win, Sherwood established himself as one of the top riders on the Red Bull X-Fighters World Tour 2009 with solid performances and including another podium finish, coming second in England.

Everything seemed to work in Sherwood's favor with a win in Moscow, and another victory in London, but then he crashed badly at the ASA World Championships of FMX in Pomona, California.

Later that year it was confirmed that Sherwood, would ride alongside FMX legend Travis Pastrana and the entire Nitro Circus crew for their huge one night only show at North Harbour Stadium on February 5, 2011.