Timmy (aka "Phantom") arrives late to register for the Pokémon Contest, because his mother gave him lots of homework to do. His father let him go, and confronts the mother when she comes to check on Timmy.
Jessie is competing under an alias in the Contest, and her Dustox takes the lead in the first round. May's Skitty fails to do a Blizzard attack, losing points and putting May behind. May still progresses to the second round.
In the second round May quickly dispatches her opponent, while Phantom beats Jessie in a tough battle. Jessie's disguise is blown off, and after losing she decides to try to steal Phantom's Dusclops instead. Pikachu sends them flying with Thunderbolt, also ripping off Timmy's mask.
Meanwhile, Timmy's father talks to his wife and brings up the fact that she only hates Pokémon because her parents took her beloved Poochyena away from her when she was a child. She relents and decides to cheer Timmy on at the Contest.
May and Timmy face off in the final round, and Skitty isn't doing so well until May instructs it to use Assist. Skitty quickly catches up and beats Dusclops. Timmy's mother encourages him to continue competing.
The Verdanturf Town Pokémon Contest is about to begin and once again May is nervous. This is the first time she will be entering with Skitty. Out in the lobby, Ash is worried because Timmy is soon going to be too late to register for the competition, but thankfully he shows up just in time. Hiding nearby, Team Rocket makes fun of Timmy for being late, since even they were able to register on time. Jessie continues to be confident that she and her Dustox will win. It later turns out that Timmy's mother was forcing him to do a lot of homework. Thankfully his father, Tommy Grimm, helped him to sneak away to the Contest Hall. At home, Timmy's mother finds him gone, and Tommy openly states that their son has left to compete in the Verdanturf Contest.
The Appeals Round begins with Jessie in disguise as "Jesslana". Her Dustox uses Poison Sting, Whirlwind, and Psybeam together with impressive effect, earning a high score of 28.5 from the Contest Judges. Following a Charizard and a Blastoise, May takes the stage with Skitty. Unfortunately their opening move, Blizzard, fails, so May tries to make up for it with Skitty using Double Slap to juggle. This works relatively well, earning her a score of 24.9. Next is Timmy in his Phantom disguise with Dusclops. Dusclops uses Will-O-Wisp and Psychic together to dazzle the judges and earn himself a 27.8. When the results are announced, it is revealed that May, The Phantom, Jesslana, and a Coordinator by the name of Stefano have advanced to the Contest Battles. Meanwhile, Timmy's parents are on their way to the Contest Hall, with Mrs. Grimm enraged that her husband would let Timmy go to a Pokémon Contest. Tommy defends his actions, saying it's what Timmy loves to do. Mrs. Grimm says Pokémon are a waste of time, but Tommy reminds her of her own involvement with Pokémon when she was Timmy's age.
Back at the Contest Hall, the second round starts with May versus Stefano and his Wartortle, who loses in a matter of seconds. Jesslana and The Phantom face off just as Timmy's parents arrive at the Contest Hall. Jessie's Dustox opens with a Whirlwind, which Dusclops counters with Shadow Punch. Dustox tries a Psybeam with much greater effect. Dustox uses Psybeam again, but this time Dusclops stops it with Psychic, causing an explosion which exposes Jesslana's disguise, revealing herself to be Jessie. The timer stops and the judges determine that The Phantom is the winner of the battle. After Team Rocket notice themselves on stage, they proceed to try and steal Dusclops. Pikachu easily stops this with a Thunderbolt, sending Team Rocket blasting off. The explosion from the Thunderbolt causes The Phantom's mask to come off, with the now-unmasked Timmy noticing that his parents are there. Much to Timmy's surprise, Mrs. Grimm apologizes and walks off. Later, backstage Tommy explains that when Mrs. Grimm was Tommy's age, she loved Pokémon too, but she was expected to take over her parents' business, so "childish" things such as her Poochyena were taken away. Her parents forbade any further contact with Pokémon. Mrs. Grimm thought that if Timmy wasn't allowed to play with any Pokémon, then he wouldn't have his heart broken like hers was. Tommy encourages his son to make the most of this chance he has in the Contest, and the final round begins.
Timmy's Dusclops starts off with a Focus Punch, striking May's Skitty. Skitty tries a Double Slap, but as a Normal-type attack, it doesn't affect the Ghost-type Dusclops. Dusclops uses another Focus Punch, but this time Skitty successfully counters with Double Slap, sending the Focus Punch back. Dusclops next uses Will-O-Wisp in combination with Psychic to further damage Skitty. Skitty tries a Tackle attack, but Dusclops counters with Hyper Beam. Skitty attempts a Blizzard, but the move fails again. Dusclops uses another Hyper Beam to damage Skitty again. Meaning to end the battle, Dusclops uses one more Hyper Beam, but May refuses to give up, this time having Skitty use Assist. The Assist creates a Gust which perfectly defends against the oncoming Hyper Beam. This defense evens out the score between the two contestants. Dusclops tries again to end the round, this time with Focus Punch, but Skitty counters with Assist again, using String Shot to stop the move.
On the sidelines, Timmy's mother is back and now encourages Timmy to win. Timmy now has enough confidence to battle without his Phantom mask. Giving it his all, Timmy has Dusclops use Will-O-Wisp. Skitty again counters with Assist, producing an Ember that stops Dusclops' attack. With another Assist, Skitty attacks with Silver Wind, but Dusclops stops it with Psychic. Dusclops again uses Hyper Beam. May decides to have absolute faith in her Skitty, and tells it to try Blizzard again. This time it works, and knocks Dusclops to the ground in defeat, making May the winner of the Pokémon Contest. Drew, who watched the Contest from the stands, is mildly impressed by May's victory over Phantom. Afterwards, Mrs. Grimm decides to allow Timmy to continue entering Pokémon Contests as long as he does not fall behind on his homework, and May receives the orange Verdanturf Ribbon, her second Contest Ribbon overall.