A Hurdle for Squirtle (Japanese: ポケモンコンテスト・ヤマブキ大会！！（後編）Pokémon Contest - Yamabuki Conference!! (Part Two)) is the 144th episode of the Advanced Generation series, and the 418th episode of the Pokémon anime. It was first broadcast in Japan on September 22, 2005 and in the United States on June 24, 2006.
The contest in Saffron City is about to begin! Harley ends up apologizing to May, but it rings hollow given his history of hating May. He goes first, and really impresses the crowd with his Cacturne's combination of Cotton Spore and Needle Arm. A disguised Jessie comes up to the stage, impressing and horrifying the crowd when she embraces James' Cacnea, followed by a firework-laden Pin Missile. May brings Combusken up, performing a great combination of Fire Spin and Sky Uppercut. All three of them make it to the next round.
Jessie and Harley are opponents next, and Jessie's strategy is to send in Wobbuffet knowing that its defensive moves could knock out Harley's Ariados. Harley is quite aware of this, and orders his Pokémon to do nothing. Frustrated and annoyed, Lillian issues them yellow cards, knocking down their points. Harley finally strikes, using String Shot to tie up Wobbuffet and move it like a helpless puppet. Eventually Wobbuffet is thrown in the air and knocked out of battle.
May makes through her next battle fine, and faces Harley in the finals. May has elected to use Squirtle, and the little Pokémon has a rough start, especially when it uses an Ice Beam that is too strong for it! Harley tries String Shot again, stringing up Squirtle near the ceiling. Ariados then uses Spider Web to cover the entire stage. May orders Squirtle to use Ice Beam again, which frees it from the Spider Web and freezes the stage—and Ariados! With the Bug-and-Poison-type out of the way, May wins the Saffron Ribbon. May is thrilled, and Ash is hyped for his next Frontier battle.
Harley is the first contestant and calls upon his Cacturne, who starts things off with Cotton Spore. The spores slowly rotate in the air while Harley calls for Needle Arm. Cacturne stands motionless for some time before suddenly protruding spikes from its whole body through all of the spores, creating an interesting display. Later, "Empress Jessibella"—Jessie in disguise—takes to the stage and sends out Cacnea. Cacnea and Jessie run toward each other and hug each other. The painful embrace moves Lilian and the crowd to tears, showcasing the pair’s close bond. Jessie tells Cacnea to use Pin Missile and the pins wind upward and collide, exploding like fireworks. Lilian goes to congratulate Jessie but notices that Cacnea is still attached to her and she's not moving at all. Lilian taps her and she falls to the floor, paralyzed with pain. Jessie is then rushed back into the operating room again by Chansey.
Lilian then introduces the last contestant, May, with her Squirtle at her side. Squirtle becomes uneasy at the sight of the massive crowd, but May says that it'll get use it. She calls upon Combusken, who emerges from its Poké Ball in a series of gymnastic somersaults. May then unties and throws her bandanna toward Combusken, ordering a Fire Spin follow by Sky Uppercut. Combusken propels the bandanna upward with Fire Spin, leaps through the spiraling flames, and uses Sky Uppercut to refold the bandana. Combusken then delivers one last blow to send the retied bandanna right back onto May's head. Combusken lands in front of May and the two pose for the finish. The crowd goes wild, shouting and cheering. Squirtle looks on admiringly and everyone seems to be pleased with her performance, except for Harley, who looks disappointed with her success.
The eight Pokémon Coordinators moving on to the Contest Battles are then announced, which include May, Harley and Jessie with the top position of the round. James and Max are surprised at Jessie's success and wonder if she might actually win. The contestants' battle match-ups are randomly selected, and it is revealed that Jessie will face Harley and May will battle a male participant in the second round of the Contest. As May is filled with excitement, Harley approaches to meddle with her confidence once again. May fires back quickly, silencing her malicious rival. Suddenly a completely bandaged individual confronts the pair before revealing herself as the "Empress Coordinator" Jessibella. Harley and Jessibella are set on defeating one another, and both point to May, declaring that they’ll beat her next.
The Battle Stage begins with Lilian introducing the first match, Jessie versus Harley. Harley sends out his Ariados while Jessie calls upon Wobbuffet. Both James and Meowth are confused by Jessie's choice of Wobbuffet for the second round. Jessie's plan is to have Wobbuffet use Counter just as Ariados fires an attack to reflect it back at double the power. Harley catches on immediately and is reluctant to make the first move, knowing it would only backfire. After neither Coordinator issues an order, Lilian announces that she has no choice but to give them each a yellow card, which subtracts half the points from both participants' scores. Contesta tells Harley and Jessie if they get another yellow card, they will both be disqualified. Both Harley and Jessie argue back and forth and Lilian is about to disqualify both of them for not battling until Harley declares that he will make a move. Upon realizing that he doesn't need to make an offensive attack, Harley tells Ariados to use String Shot on Wobbuffet. Seizing the opportunity, Jessie directs Wobbuffet to use Counter, but Wobbuffet becomes helplessly wrapped by the threads. Harley explains that Mirror Coat and Counter will not work against defensive moves, a strategy that Brock commends. Ariados then manipulates Wobbuffet like a puppet with its attached strings, as points are gradually deducted from Jessie's score. The crowd begins to laugh at the puppet show on display, which is ended when Ariados tosses Wobbuffet. The rest of Jessie's points are deducted and Harley advances to the next round. Jessie, James, and Meowth then fall to the ground, turning white from disbelief.
May breezes through the next rounds with Squirtle defeats a Crobat with Bubble followed by Squirtle knocks out a Weepinbell with Tackle. Similarly, Ariados entangles a Walrein in a Spider Web. With both May and Harley having won all their rounds, they find themselves in the finals of the Saffron Contest.
Lilian starts the final match as May calls out Squirtle and Harley brings out Ariados. Ariados attaches itself to the ceiling with its String Shot and swings into frighten Squirtle with a Scary Face. Squirtle then recovers and uses Ice Beam on Ariados, but it is so powerful that it misses its mark and knocks Squirtle onto its back. Ariados then retracts up to the ceiling and shoots another String Shot onto Squirtle's body, reeling it in and deducting more of May's points. Harley decides to rack up style points by covering the whole stage with Spider Web, impressing Lilian and the audience. Ariados then spins Squirtle around in a circle and sends it hurtling onto the web, entangling its back in the process. As Squirtle continues to struggle, May's points are approaching zero. Ariados then descends down from the ceiling to the web and begins walking towards Squirtle to strike with Double-Edge. May tries a Bubble attack, but it doesn't even slow Ariados down.
May then recalls Squirtle's last attempt of Ice Beam which propelled it backwards, and uses it to free Squirtle from the web. The attack also freezes Ariados and the web, leading Harley's points to drop by more than half. Squirtle runs and jumps onto the frozen web to hit Ariados with Bubble, shattering the ice and throwing Ariados backward. Ariados tries to stop itself, but its feet can't get any grip on the frozen web. Squirtle slides down the icy webs like a surfer and Tackles Ariados to the ground, knocking it out. Squirtle neatly lands on its feet on top of Ariados. With Ariados unable to battle and May is declared the winner. Squirtle comes running back to May for a hug as Ash, Brock, and Max cheer from the stands. Harley thinks that the Contest was rigged and walks off in a huff. The crowd cheers as May is awarded her first Kanto Ribbon, making for a great start to her Kanto Contest campaign.