May is feeling the pressure at the Mulberry City Pokémon Contest, her last chance to get a fifth ribbon before the Grand Festival. To make things worse, Harley shows up! He has his ribbons already so he doesn't have to compete. But Jessie plans to enter in her Jessebella disguise, so when Harley spots Team Rocket, he offers to loan them his Cacturne and Banette to use against May in the Contest.
The Contest begins, and Jessie does great with Cacturne. May and Combusken then take the stage, but unseen by anyone, Harley's Ariados secretly trips up their grand entrance with its webs. Pikachu and Ash sense something's afoot and head to the stage rafters, where they find James, Meowth, and Ariados. Meanwhile, Combusken's Fire Spin display sets Ariados' webs on fire and soon, with Pikachu's help, Team Rocket's plans are up in smoke! May makes a quick recovery and her performance has Harley steaming.
With that round over, Jessie and May advance to the second round. Harley is furious at Team Rocket for messing up the plan, but he's not done messing with May yet. What underhanded tricks will he and Team Rocket come up with in the next round of the Contest...?
Nurse Joy and Chansey return May's Pokémon to her as she is preparing herself for the upcoming Mulberry City Pokémon Contest. Joy also reveals that the Mulberry event is the last Contest to be held prior to the Kanto Grand Festival in a month's time, and therefore her last chance to obtain her fifth Ribbon. The news instantly puts pressure on May, making her nervous about the upcoming Contest. May jumps out of fear as her rival Harley approaches from behind. Harley deliberately drops his Ribbon case, and as May open it she is stunned to learn that he already has five Ribbons. Harley looks forward to seeing May loses and walks off having left May furious. Brock remarks that at least Harley is good for something as May orders Ash outside for some training.
Jessie debuts her rather-expensive Contest attire as "Jessibella" as she selects Meowth for the Mulberry Contest. She imagines that Meowth’s talking will make for a wonderful comic Appeal, though he slashes her dreams to shreds. Jessie is furious, but her anger is interrupted by Harley. He grabs a hold of Jessie's hand, admitting he is a big Jessibella fan. Harley shows his five Ribbons to Team Rocket and pledges his support to help Jessie to defeat May in the final Contest. The trio are curious as to why Harley would want to help them. Harley recounts that when he was at school he almost finished his last piece of food, when a girl resembling May grabbed a piece of food resembling an Octillery. As the girl walked off into the distance displaying her pleasure, Harley was left broken and became set on getting his revenge. Jessie is overwhelmed by Harley's story and agrees to assist him. Harley then calls upon his Banette and Cacturne to assist Jessie in claiming the final Ribbon required by May. Cacturne takes a liking to Jessie and clamps onto her body, showing its approval.
Lilian begins the Contest preparations by introducing the Contest Judges, and displaying the final Ribbon up for claim. As Lilian begins the Contest, Drew steps inside the stadium to view the contestants' progress. The first round of contestants include Altaria, Clamperl, Koffing, and many more. Jessie finally makes her appearance with Cacturne. Jessie throws a vegetable into the air as Cacturne dices it into a small structure using its extended needles. The crowd applauds Jessie and Cacturne's display of skill. Cacturne follows up by releasing Cotton Spore before shooting them down with Bullet Seed for a magnificent shower of sparkle and shine. All three judges show their approval as Harley claps for Jessie.
May makes her Contest appearance as she begins to rotate to unleash her Poké Ball, but manages to slip and fall to the ground. Above the stadium, Meowth and James are controlling Ariados using its sticky web to cause May and her Combusken to lose their balance and fall to the ground. May runs to Combusken's side, but is tripped once again. As Ariados's web grasps onto Combusken once more, it becomes temporarily visible as Pikachu point the fault out to Ash. Pikachu and Ash rush up to the ceiling and quickly discover Team Rocket are behind May’s disastrous Appeal. Pikachu rushes forward with Quick Attack, though Ariados manages to stop pin him to the handrail with its web. Combusken begins rotating at a high speed using a Fire Spin attack. The twirling flames combine with Ariados's web for an incredible display of control, impressing the judges, though infuriating Harley. As James and Meowth continue bickering, the flames finally reach the stadium ceiling and engulf Ariados. James and Meowth move to attempt to put the fire out, though the embers scorch through Pikachu's restraint. Meowth extends his claws and dashes forward while Pikachu counterattacks with a devastating Iron Tail blasting James, Meowth, and Ariados through the stadium ceiling. Combusken bursts into the air as May throws the frisbee into the air. Combusken returns it back to her with a brilliant Sky Uppercut and Mega Kick. Combusken lands elegantly to the ground as the three judges offer their overall positive opinions. Backstage, May remains doubtful that her Appeals performance was enough. Ash arrives to announce to her that Team Rocket was trying to eliminate her in the first round. The television screen lights up and Lilian announces the eight Pokémon Coordinators moving on to the Contest Battles including Jessie and May.
Meanwhile, Harley soothes his Ariados from its battle wounds. He turns his attention to the Rocket trio, scolding them for their poor efforts and failing to eliminate May from the Contest. With an extension of his arm, Harley returns his Ariados to its respective Poké Ball and stampedes out of the room. Even so, Jessie is determined to win and smirks as she considers her plan of revenge against May.