MacDonald made his UFC debut on October 10, 2006, at Ortiz vs. Shamrock 3: The Final Chapter against the favored The Ultimate Fighter 3 finalist Ed Herman. In an upset, MacDonald won the bout via triangle choke in the first round. MacDonald followed up the performance with a win over The Ultimate Fighter 1 veteran Chris Leben via modified guillotine choke in the second round. Both victories earned Submission of the Night honors.