James disguises himself as Jessilina and participates in his first Pokémon Contest.
With the exception of those owned by main characters, all of the Pokémon that entered in the Lilypad Contest were introduced in Generation II.
James's win of the Lilypad Contest marks the first time a main character participated in a Pokémon Contest and won it on their first try.
In addition, it also marks the first time James has cross-dressed in Pokémon the Series: Diamond and Pearl, something that used to be a frequent running gag for him in previous anime seasons.
James wins the Lilypad Contest on Jessie's behalf, earning Jessie her third Contest Ribbon.
Dawn competes in the Lilypad Contest, but loses in the semifinals, suffering her first loss to Jessilina.