The night before the Contest, Drew trained with Masquerain, who used Quick Attack, followed with Bubble. May approached Drew and both showed they obtained new Pokémon, as May recently caught a Bulbasaur. During the Rubello Contest, Drew sent Masquerain to battle Sonny's Girafarig. Girafarig attacked with Iron Tail, which Masquerain dodged. Masquerain emitted some bubbles, then froze them with Ice Beam. Masquerain used Hidden Power, causing the attack to bounce off the icy spheres and fall onto Girafarig, defeating it in an instant. During the final round, Masquerain battled against Savannah's Lairon. Masquerain dodged its Metal Claw attack and defeated Lairon with Hidden Power, thus making Drew the winner of the Contest.
Drew was training with his Masquerain, who used Silver Wind on the waves, before being approached by the heroes. After infuriating May with his comment, Drew faced her in the battle, using Masquerain against her Beautifly. Just as they exchanged Silver Wind attacks, Team Rocket appeared and sucked both Pokémon into the submarine. By accident, they also sucked the heroes in, so May and Drew called Beautifly and Masquerain into their Poké Balls. Later on, Drew sent Masquerain, who used Silver Wind to negate Jessie's Dustox's Poison Sting and blasted Team Rocket off with the same attack, though it was assisted by May's Beautifly.
During the Grand Festival, Drew was preparing Masquerain for the appeals round. In that round, he had Masquerain use Hidden Power to spread the sprinkles. Next, Masquerain used bubbles to spread around the stadium, then used Silver Wind to burst them and captivate the audience, earning him a perfect 100 score. The next day, he faced Robert in the Grand Festival. However, Robert's Milotic's Twister and Claydol's Hyper Beam quickly defeated his Masquerain and Flygon. At evening, after the Grand Festival was over, Drew went back to training. His Roselia attacked Masquerain, who was struck down, to which Drew told Masquerain it should've dodged that attack.
During the Kanto Grand Festival, Drew sent Masquerain for the appeals round. It used Silver Wind to emit a beautiful display, earning him the victory and advance to the next round. Masquerain, along with Roselia, battled a Coordinator's Loudred and Medicham in the following round, earning Drew another victory.