[5] Gracie signed with Art of War Fighting Championship and made his debut on May 23, 2009, where he defeated in a mixed martial match Magomedbag Agaev from Daghestan at 5:09 seconds in Round 1.
[1] Rolles, in his second fight for the Art of War FC promotion, defeated K-1 kickboxing veteran, but at the time 0–2 in MMA, Peter Graham early in the first round.
[9] Following the defeat, Renzo Gracie described Rolles' performance as "embarrassing", saying his exhaustion was caused by nerves and the pressure he put on himself.
Rolles faced Tony Bonello in a Heavyweight bout at ONE FC: Pride of a Nation in Quezon City, Philippines.
[18] He then faced former Polish strongman and five-time World's Strongest Man winner Mariusz Pudzianowski at KSW 31 on May 23, 2015.
[22] A rematch between the two teams took place on February 11 at The New Beginning in Osaka and saw Rolles submit Sakuraba for the win.
[23] On April 6 at Invasion Attack 2014, the Gracies defeated Takashi Iizuka and Toru Yano in another tag team match.
[citation needed] He also owns and operates the Rolles Gracie Academy in Old Bridge, New Jersey and West Long Branch, NJ.