first six Ultimate Fight Night events, during which he earned a string of victories: a split decision win over future TUF 4 finalist Patrick Côté, an armbar submission against Edwin Dewees, a first-round TKO over Jorge Rivera, and a unanimous decision over Luigi Fioravanti. Leben was defeated by Anderson Silva at UFC Ultimate Fight Night 5 on June 28, 2006, by KO 49 seconds into the first round, but returned at UFC Fight Night 6 on August 17, 2006, where he defeated Jorge Santiago by knockout 35 seconds into the second round. He is the only fighter to fight at every event under the "Fight Night" banner. Leben then lost at UFC 66 to longtime UFC veteran Jason MacDonald via technical submission due to a modified guillotine choke with less than a minute remaining in the second round. Leben then lost to Kalib Starnes by a very close unanimous decision at UFC 71 on May 26, 2007. The bout won Fight of the Night honors. It was reported that Leben was offered a main event fight against Mike Swick at UFC Fight Night 11, but turned down the fight for unknown reasons; it was later revealed on the Ultimate Fighter Season 1 reunion show by UFC President Dana White's call to matchmaker Joe Silva that Leben's camp turned down the fight and that Leben himself had no prior knowledge of the fight offer. Leben instead took on Terry Martin on the same UFC Fight Night 11 card. Even after being rocked with multiple punches by Martin, a half-dazed Leben defeated Martin by knockout at 3:56 of the third round. At UFC 82, he knocked out Italian Alessio Sakara in the first round, winning the Knockout of the Night award. On April 30, 2008, Leben was arrested in Oregon by Clackamas County Sheriffs for a DUI stemming from an earlier date. He was kept in jail and temporarily held without bond for allegedly violating his probation. Leben was then sentenced to 35 days in jail. His next fight was against Michael Bisping at UFC 89, which he lost by a unanimous decision after a full three rounds. Leben taunted Bisping throughout the last two rounds by dropping his arms and raising his chin. The judges scored the fight 30–27 (twice) and 29–28 for Bisping. Bisping used effective counter punching in the fight to keep the aggressive Leben at bay. Both fighters