Simons' attempt to kiss the rim on his final dunk earned him three of five votes from the judges. He's the first player in Trail Blazers history to win the competition.
"In practice, I never actually kissed the rim, but I was like, 'I gotta commit to it,'" Simons said following the contest, according to ESPN's Andrew Lopez. "I tried to put a mouthpiece in last-minute, but it didn't fit in my mouth.
"I just scratched, and I'm just going to emphasize the smooch face so people know I'm next to the rim and trying to kiss it."
Simons paid homage to Tracy McGrady with his last first-round dunk, donning McGrady's vintage Toronto Raptors jersey and replicating his 360-degree slam from the 2000 Slam Dunk contest to earn a spot in the final round. The jam gave Simons the highest score of the evening (49).
Toppin punched his ticket to the championship round by leaping over teammate Julius Randle and his father en route to a one-handed windmill slam.
Indiana Pacers guard Cassius Stanley was eliminated in the competition's opening round after posting the lowest two-dunk score. Despite failing to advance, the Duke product had arguably one of the best dunks of the night.
The second-round pick kicked off the contest with a between-the-legs jam, but he only earned a score of 44.