Gracie stepped into the
International Fight League for his first MMA fight on the undercard of the IFL World Team Championships in 2007. He joined his cousin
Renzo Gracie's
New York Pitbulls in the IFL. Gracie's younger brothers Igor and Gregor are also mixed martial artists. Gracie was set to fight
Ricardo Romero at Ring of Combat 24, April 17, 2009, but he withdrew from the fight a week before due to an injury sustained in practice. 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. 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.
Ultimate Fighting Championship Gracie was expected to make his
UFC debut on February 6, 2010, in
Las Vegas, Nevada against
Mostapha Al-Turk Due to
Mostapha Al Turk having visa troubles, Gracie instead faced
Joey Beltran in his UFC debut. Gracie secured a takedown early, and managed to take Beltran's back. However he would quickly become exhausted, and Beltran would defend the rest of his takedowns with ease. In the second round, Gracie attempted another takedown but was denied, and Beltran immediately started landing ground and pound which Gracie was unable to defend, causing referee
Herb Dean to stop the fight. 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 was released from the UFC after just one fight.
Post-UFC Gracie was to face Mike Ciesnolevicz at a Shine Fights event on January 8, 2011. The event, however, did not materialize. Instead, Gracie made his first post-UFC appearance on April 22, 2011, at UCC 4: Supremacy. He defeated Braden Bice via submission in the first round.
ONE Fighting Championship On December 8, 2011, it was announced that Gracie had signed for Asian promotion
ONE Fighting Championship. He made his debut at
ONE FC: Battle of Heroes in Jakarta, Indonesia on February 11, 2012, where he took on
Bob Sapp. Gracie won the fight in the first round by submission due to strikes. Rolles faced Tony Bonello in a Heavyweight bout at
ONE FC: Pride of a Nation in Quezon City, Philippines. He won via submission in the third round.
World Series of Fighting Gracie was set to take on Dave Huckaba at
WSOF 3 on June 14, 2013. However Gracie was forced out of the fight due to a wrist injury. In his promotion debut, Gracie faced
Derrick Mehmen on
WSOF 5 on September 14, 2013, at
World Series of Fighting 5: Arlovski vs. Kyle, where he was knocked out in the second round after outboxing Mehmen in the first.
KSW After signing with the Polish MMA promotion
KSW, Gracie challenged Karol Bedorf for the KSW Heavyweight Championship at
KSW 28 on October 4, 2014. He lost the fight by TKO in the first round. He then faced former Polish strongman and five-time
World's Strongest Man winner
Mariusz Pudzianowski at
KSW 31 on May 23, 2015. Gracie lost in surprising fashion by KO after Pudzianowski landed a punch just 27 seconds into the first round. ==Professional wrestling career==