Wineland was scheduled to face Rafael Rebello on January 10, 2010 at WEC 46, but Rebello was forced off the card with an injury and replaced by George Roop. He won via unanimous decision.
Wineland was scheduled to face Charlie Valencia on June 20, 2010 at WEC 49, but Valencia was forced off the card with an injury. Wineland eventually faced Will Campuzano. Wineland defeated Campuzano via second-round TKO, earning Knockout of the Night honors.
Wineland was expected to face Damacio Page on November 11, 2010 at WEC 52. However, Wineland was forced out of the bout with a shoulder injury and replaced by Demetrious Johnson.
Wineland then faced Ken Stone on December 16, 2010 at WEC 53. He won via KO due to a slam in the first round, earning his second straight Knockout of the Night award.
On October 28, 2010, World Extreme Cagefighting merged with the Ultimate Fighting Championship. As part of the merger, all WEC fighters were transferred to the UFC.