After narrowly managing to get into the Saffron City contest, May has her work cut out for her when she has to take Combusken and Squirtle to their limits in dealing with Harley and a disguised Jessie.
- Color Failure: Jessie ends up like this when Wobbuffet loses to Harley's Ariados. James and Meowth follow suit shortly thereafter.
- Curb-Stomp Battle: The moment Ariados strings up Wobbuffet, Jessie goes down without even blinking.
- Dick Dastardly Stops to Cheat: Averted. Jessie surprisingly restrains herself when in the contest, and only loses because she underestimated Harley's cunning against her Wobbuffet. Brock suspected Harley was cheating, but he was just that good. Harley, upon his defeat, thought May only won because she cheated.
- "Eureka!" Moment: May is hesitant to use Squirtle's ice beam attack again when it's all she has left against Harley's Ariados, due to the attack being too powerful. She then realizes it's her best chance, and him using it not only free's Squirtle, but it ends up freezing the entire webbing Harley had Ariados spray all over the arena, leaving the spider unable to safely maneuver around the field.
- Hoist by His Own Petard: Jessie tries using Wobbuffet to deflect Ariados' attack back at him, but Harley sees right through it. When both are almost eliminated for not attacking, Harley uses a defensive attack to get past Mirror Coat and Counter, turning the poor Pokemon into a puppet before knocking him out.
- Loophole Abuse: Harley's Ariados can't attack Wobbuffet because any offensive move will be redirected by Counter or Mirror Coat. However, he figures out that he can use the non-offensive String Shot to yank Wobbuffet around like a marionette on strings and fling it across the arena.
- Meat Puppet: How Harley's Ariados beats Jessie's Wobbuffet.
- Shocking Elimination: In-Universe, it's very narrowly averted. The judges almost remove both Harley and Jessie from the contest when both parties refuses to make a move, but Harley just goes ahead with a defensive attack (String Shot) to keep himself in the match.
- Sore Loser: Harley's convinced May only won because she cheated.
- Won't Get Fooled Again: Harley tries pulling his Nice Guy act on May, acting as if he accidentally gave May bad information. She doesn't fall for it, and he reverts right back to his Jerkass persona right away the moment she calls him out.
