The group arrive on Navel Island where Ash finds himself up against the Gym Leader, Danny as Ash competes for his second Orange League badge. Misty tries to tempt Ash by showing more caring attitude to Danny. Ash once again gets jealous and sad.

The episode was rated 7.60 from 116 votes.

Still on Mandarin Island, Ash and his friends go through Victorian Town where they find two Nidoran who are in love with each other but any possible hint of a relationship is being derailed by the trainers who happen to be childhood rivals.

The episode was rated 7.62 from 108 votes.

Arriving on Murcott Island, Ash and his friends discover a wounded Scyther. After capturing it, Tracey must take it to a Pokémon Center. While there, he discovers the Scyther got dethroned from being in charge of his group.

The episode was rated 7.63 from 112 votes.

Ash arrives on Trovita Island prepared to battle for his third Orange League Gym Badge. However, much to Ash's dismay, the Gym Leader, Rudy has more than just battling on his mind, Rudy develops a crush on Misty, and Ash gets jealous once again. Rudy moves in to court Misty after she helps rescue his younger sister, Mahri. While Ash battles for the Spike Shell Badge, Misty considers the tempting offer to stay on the island with Rudy and Mahri forever.

The episode was rated 7.64 from 108 votes.

Just as Ash, Misty, and Tracey set foot on Mandarin Island, Pikachu and Togepi turn against them and join a group of other angry Pokémon. When the misbehaving Pokémon disappear, Officer Jenny arrives and informs them that dozens of Pokémon have been reported missing, including Meowth! Everyone fears a Psychic attack is behind this mystery. Will Jessie and James actually join forces with our heroes? Could they possibly win a battle for the first time?

The episode was rated 7.66 from 140 votes.

The group descend on Mandarin Island where Ash's arrogance emerges due to the fact that he's won every single battle he's had since arriving on the island but upon meeting Prima, a member of the Elite Four and challenging her to a battle, Ash starts to realize that he may have made a grave mistake.

The episode was rated 7.68 from 107 votes.

After Gary saves the day against Team Rocket, Ash decides to challenge him where Pikachu is against Eevee. However, Gary wins the battle. Ash is depressed, but goes to follow Gary to Johto in order to beat him once and for all. Tracey decides to stay in Pallet Town, so he can be Professor Oak's assistant. In the end, Brock rejoins the group and they head off to Johto.

The episode was rated 7.70 from 102 votes.

Ash, Misty and their new friend, Tracey, are on a new adventure exploring the Orange Islands as Ash sets out to qualify for the Orange League Tournament. After hearing that the Mikan Gym Leader is known as one of the toughest trainers in the Orange Crew, Ash can't wait for the challenge. He learns that Pokémon battles are run a little differently on the Orange Islands, but he can always rely on his Squirtle to pull them through!

The episode was rated 7.73 from 139 votes.

Arriving on the Grapefruit Islands, Ash discovers that there is a Snorlax going from island to island eating all the grapefruits. Ash is employed to help stop the Snorlax, but the Snorlax proves to be slippery. Later on, Ash captures the Snorlax.

The episode was rated 7.73 from 128 votes.

Having been crowned the Orange League Champion after winning his battle against Drake, Ash and the team are heading back to Pallet Town in Kanto but their plans get derailed when Lapras finally discovers its family, only for everyone to realize that Lapras's pack want nothing to do with Ash's Lapras now that it has gotten involved with humans. Ash, Misty and Tracey soon learn that a group of pirates and their Tentacruel are attacking Lapras's group and when the bullying starts up again, with Tracey having gone to alert Officer Jenny, Ash and Misty decide to get into the fight, vowing to stop the pirates once for all.

The episode was rated 7.77 from 108 votes.

On Kumquat Island, Ash discovers Luana, the final Orange Island Gym Leader, who mistakes him for her son. After defending the island from Team Rocket, they head to the Gym to have a Double Battle where Pikachu and Charizard battle against Marowak and Alakazam but Pikachu's and Charizard's unwillingness to work together might end up costing Ash his chance of qualifying for the Orange League.

The episode was rated 7.78 from 108 votes.

After getting his 3rd Orange League Badge, Ash and his friends arrive on an island, where Pikachu is soon captured by Team Rocket and is chained to Meowth. But soon after Pikachu and Meowth are taken away by a giant Pidgeot, the trapped rivals eventually learn how to get along.

The episode was rated 7.78 from 105 votes.

Having arrived on Pumello Island, Ash finally gets the chance to battle the Orange League leader and Champion, Drake in a full six-on-six Pokémon battle, only to discover that the battle may prove to be the toughest one he's ever had.

The episode was rated 7.80 from 102 votes.

Ash, Tracey and Misty are sailing along on Lapras when they almost crash into another Pokémon trainer wanting to battle Ash. This trainer heard about Ash from the Trovita Island gym leader and wants to put his Pokémon up against Ash’s. When the new trainer uses a super-powerful Poliwrath on Charizard, it’s more than anyone expects. After Charizard gets frozen in a battle, Ash tries to defrost him. Charizard, still distrusting of Ash, doesn't want his help, but Ash keeps trying. Charizard finally decides to obey and respect Ash as not only his trainer but also his friend, and the two become closer than ever! Ash is able to give a stunning defeat to the Poliwrath that froze Charizard earlier.

The episode was rated 8.06 from 115 votes.

Ash continues his fight against Drake in hopes of becoming the Orange League Champion and earning a place in the Orange League Hall of Fame but things hit a snag when Drake brings out his final Pokémon—the legendary Dragonite whose overwhelming strength and powerful attacks are a force to be reckoned—causing Ash to realize that his dream of becoming Orange League Champion may not become a reality after all.

The episode was rated 8.25 from 122 votes.