The Pokémon Contest in Verdanturf Town 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 nervous because Timmy is soon going to be too late to enter the Contest, but thankfully he shows up just in time. Hiding nearby, Team Rocket make fun of Timmy for being late, since even they were able to register on time. Jessie continues to be confident that her and her Dustox will win.
Turns out his mother was forcing Timmy to do a lot of homework. Thankfully his father, Tommy Grimm helped him to sneak away to the Contest. At home, Timmy's mom finds him gone, and Tommy openly states that he's at the Contest.
The Contest opens with Jessie in disguise, earning some good opening points with her Dustox. Dustox uses Poison Sting, Whirlwind, and Psybeam together with impressive effect, earning high points from the 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 DoubleSlap to juggle. This works relatively well, giving May a decent enough score to move on to the second round.
Next is Timmy in his Phantom disguise with Dusclops. Dusclops uses Will-O-Wisp and Psychic together to dazzle the judges and earn a high score.
Meanwhile, Mrs. Grimm and Tommy are on their way to the Contest, with Mrs. Grimm enraged that her husband would let Timmy go to the 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, the second round starts with May versus Stefano and his Wartortle, who loses in a matter of seconds. Jessie and Timmy then face off just as Timmy's parents arrive at the Contest. 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 Jessie's disguise. The judges determine that Timmy is the winner of the battle, so Team Rocket try to steal Dusclops. Pikachu easily stops this with a Thunderbolt, sending Team Rocket blasting off again.
The explosion caused by the Thunderbolt causes Timmy's Phantom mask to come off, and Timmy suddenly notices that his parents are there. Much to Timmy's surprise, Mrs. Grimm apologizes and walks off. Later, Tommy explain 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 of the Contest begins.
Timmy's Dusclops starts off with a Focus Punch, hitting Skitty. Skitty tries a DoubleSlap, 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 DoubleSlap, 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 tries 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 Hyper Beam. This defense evens out the score between the two Contestants. Dusclops tries again to end the battle, this time with Focus Punch, but Skitty counters with Assist again, creating a 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 ends the battle with Dusclops, making May the winner of the Pokémon Contest!
Mrs. Grimm decides to allow Timmy to continue entering the Contests as long as he doesn't fall behind on his homework, and May receives her second Contest Ribbon.
- Featured Pokemon: Wooper, Spheal, Delcatty, Zubat