Riddle's UFC career got off to a promising start: he won his first three fights in the promotion before losing a bout to Nick Osipczak in England. He bounced back with two more wins, though one was a DQ win due to an illegal upkick. And despite hitting a two-fight slump in 2010/2011, the news wasn't all bad: Riddle's match against Sean Pierson in Montreal was a classic brawl, and his following bout with Lance Benoist won him Fight of the Night honours, along with a $55,000 bonus. At that point, had Riddle's UFC career carried on, he may have found himself in the bottom half of the top ten before too long. However, things unfortunately didn't go as planned, and the wheels began to come off. Riddle would secure one more win at UFC 142 in 2012 before hitting a storm of controversy.