Jessie/Anime/Main series/History/DP

In Two Degrees of Separation!, approved the trio's plans to set up Team Rocket in Sinnoh.

In Mounting a Coordinator Assault!, Jessie disguised herself as Jessilina (Japanese: キャンディ・ムサリーナ Candy Musalina) in order to compete in the Jubilife City Pokémon Contest. When the results were announced in Arrival of a Rival!, it was shown that Jessie's performance had secured her a place in the second round, where she lost to Zoey and her in the finals. The disguise adopted for the Jubilife Contest was used in every official Pokémon Contest Jessie entered in the Sinnoh region and the Hearthome Collection as well.

After rescuing Ash's Aipom from falling off a cliff in Borrowing on Bad Faith!, Jessie managed to persuade to let her borrow Aipom for an informal Pokémon Contest that would be held in a small village as part of a festival. Jessie then decided to practice for the competition, asking Aipom to show off all of her moves. Jessie's session paid off as she easily advanced to the second round of the Contest, where she faced  and her. During their battle, Jessie used a Contest combination to drop Dawn's points before commanding Aipom to attack Pachirisu with, which caused the Pokémon to faint, thereby eliminating Dawn from the Contest and giving Jessie her first Contest victory.

In Team Shocker!, Jessie entered the Contest with her. Their performance left the three judges, Raoul Contesta, Mr. Sukizo, and Nurse Joy, very impressed as and  were in sync with one another. This secured Jessie a place in the Battle Round, where she quickly made her way to the finals. There, Jessie faced and his  using her Dustox. She was able to win the battle by taking advantage of Kenny's techniques, having used Prinplup's moves to favor her Dustox. This victory gave Jessie her first Ribbon.

In Crossing Paths, Jessie was in the middle of a training session on the shores of a mountain lake when her Dustox got distracted and flew away. Jessie hurried after her and found her with a  belonging to a  named Austin. Austin told Jessie about the Dustox Crossing, a time when Dustox gather at the lake and pair up before flying over Mt. Coronet towards the Dustox Flower Field, where they start their families. After hearing this and noticing her Dustox's crush on Austin's Dustox, Jessie remembered her school days when she had a crush on a boy called Astin. One day, Astin decided to leave town to become a and invited Jessie to come along with him, but Jessie declined the offer. To this day, Jessie wonders how her life would have turned out if she had joined Astin in his. Jessie was determined to prevent Dustox from making the same mistake, and decided to her so she could take part in the Crossing with Austin's Dustox. When Dustox refused to leave, Jessie broke Dustox's, telling Dustox to go follow its heart. As Dustox fluttered off with her partner, Jessie remembered their time together before calling out to Dustox telling her to go fall in love with all of her heart and to do it for the both of them.

In Our Cup Runneth Over!, Jessie announced her plans to enter the Wallace Cup and said she would dedicate her performance to her released Dustox. She also decided to go looking for Wallace, thinking that meeting Wallace would increase her chances of winning the special Pokémon Contest bearing his name. After finding him, she showed him her dressed up as a  and asked him to award her some bonus points during the Wallace Cup. She later watched as Wallace delivered a performance with his Milotic, and asked him to teach to her Seviper, but Wallace said Seviper could not learn the move.

When Jessie entered the Wallace Cup in Staging a Heroes' Welcome!, she was counting on James and to make sure she would be the one taking the  home, as she believed they had plotted a scheme for her to win the Solaceon Town Pokémon Contest. However, they admitted to her that they did not use any cheats back then and told her that she won the Solaceon Ribbon all by herself thanks to her skills as a Pokémon Coordinator. Later, Jessie used in the first round of the Wallace Cup. She started the performance by running towards Wobbuffet while he ran at her using. When the two collided in the middle of the stage, Jessie was sent flying in the air. She then finished it off by landing on top of Wobbuffet's head, but failed to impress the panel of judges. For this reason, Jessie didn't make it past the Performance Stage. Jessie then reappeared in the Wallace Cup in her Contest announcer persona "Jessadia", interviewing Coordinators backstage.

In Shield with a Twist!, Jessie found out a Pokémon Contest would be held in Majolica Town and decided to participate. After advancing to the second round, where she managed to defeat all of her opponents, Jessie won the prestigious Majolica Ribbon, her second Contest Ribbon overall.

In Dressed for Jess Success!, Jessie was determined to win her third Contest Ribbon. However, she was sick and unable to take part in the Contest, so she persuaded James to go dressed as Jessilina and compete in her place. She watched the whole competition on television, in which James managed to defeat in the semifinals.

Jessie competed against several Coordinators in the Neighborly Town Pokémon Contest in Teaching the Student Teacher!. She made it through the Performance Stage and managed to defeat each one of her opponents in the Battle Stage, winning the event with the help of her Seviper and earning the Neighborly Ribbon, her fourth Contest Ribbon overall.

In Dawn of a Royal Day!, Jessie entered the Contest hoping to win her fifth and final Ribbon. Not knowing that Dawn and Princess Salvia had switched places for the day, she was puzzled when she saw Dawn backstage, as Dawn had already completed her requirement to compete in the Grand Festival. During the first round, she delivered a performance that assured her progression to the Battle Stage. There, she quickly made her way to the finals, where she found herself up against a disguised Salvia. Using her Seviper against Salvia's Togekiss, Salvia was able to make a comeback after hearing some encouraging words from the real Dawn, defeating Jessie and earning the Arrowroot Ribbon. Later, Salvia approached Jessie backstage and gave her the Contest Ribbon as a token of gratitude for their battle in the finals. Jessie was confused and furious for receiving what she called a pity Ribbon. She was about to throw away the Ribbon but James convinced her to keep it so she could take part in the Grand Festival; as she had obtained her fifth Contest Ribbon fair and square, she was now qualified to compete.

Jessie entered the Sinnoh Grand Festival in Last Call — First Round!. When the results were announced, it was revealed that Jessie was among the 32 Coordinators advancing to the Contest Battles. In Opposites Interact!, she defeated her first opponent in the Battle Stage with the help of her Yanmega and Seviper. After advancing to the semifinals of the competition in Coming Full-Festival Circle!, she used her Seviper and Carnivine to face off against Dawn and her and. Despite her efforts, she ended up losing the battle.

After her loss to Dawn, Jessie got furious as her dream of becoming was destroyed. Regardless, she told Dawn that since she had been defeated by her, she wouldn't forgive her for as long as she lived if Dawn didn't end up as Top Coordinator, thus showing that Jessie was rooting for Dawn despite the two being rivals. When Dawn lost to Zoey in the finals of the Grand Festival in A Grand Fight for Winning!, Jessie was enraged and decided she was done with Pokémon Contests. She then discarded her Jessilina costume before storming away. None of the main characters ever learned that Jessie and Jessilina were the same person.