Crutchlow moved on to manufacturer-cup racing, earning the Aprilia RS 125 Challenge title in 2001 and finishing runner-up in the Yamaha R6 Cup in 2003. The next year saw him enter the British Supersport Championship aboard a Honda, beginning a three-year stint that culminated in winning the 2006 national championship.

That earned Cal a move up to British Superbike the following year with Rizla Suzuki, and his debut season saw him score a pole position at Croft and a podium finish at Brands Hatch, ultimately finishing ninth overall. For 2008, Cal switched back to Honda machinery with the HM Plant squad, where his performance immediately took a step forward, and thanks in part to a pair of victories, he finished the year third in the standings.

The following year saw Crutchlow advance to the international stage, where he found immediate success. After accepting an offer from the factory Yamaha team to campaign the Supersport World Championship, his consistently fast pace and strong results helped him to earn the title in his debut year.

The accomplishment earned him a promotion to the Superbike World Championship in 2010, and his rookie season saw him take a trio of victories, plus an additional eight podium finishes, as he rode to fifth position in the final standings.

Once again, Cal was rewarded, this time with a move to MotoGP with Monster Yamaha Tech 3. Crutchlow immediately set to work adapting his riding style to the new class as he rode to twelfth place in the championship, earning Rookie of the Year honours along the way. With a year of experience under his belt, Cal stepped up his performance in 2012, regularly posting top-five finishes and-in the latter part of the season-collecting a pair of podium finishes as well.

That set him up for an even better 2013, as Crutchlow earned the first two MotoGP pole positions of his career and also posted two runner-up finishes and a pair of third-place results. At year's end, he was an impressive fifth in the points standings, the best of the non-factory riders.

Crutchlow's abilities were not lost on the Ducati Team, and for 2014, the Briton was hired by the Italian manufacturer to race as a factory rider alongside Andrea Dovizioso aboard the Desmosedici.