Fernández played in his first regular-season NBA game on October 28, 2008, coming off the bench to score 16 points in a 96–76 Portland loss to the Los Angeles Lakers. On November 12, 2008; Rudy scored 25 points in 29 minutes against the Miami Heat, including 8 of 8 from the free throw line adding to his already 92% FT shooting to set a new NBA career high. On January 18, 2009, it was announced that Fernández had won the fan voting and was picked the fourth dunker to go to the NBA Slam Dunk Contest as part of the 2009 All-Star Weekend. During the contest, he paid tribute to the late Trail Blazer Fernando Martín by wearing his #10 jersey. Fernández was eliminated in the first round of the competition, after what some thought was biased judging.