• Air date: 28 Jan '99 36 episodes
      Ash’s journey to the top of the Indigo League continues—but will his friendship with fellow Pokémon League competitor Richie endanger his chances? With his Kanto journey completed, Ash finds there’s still plenty to see and do when Professor Oak sends him and his friends to the Orange Islands. Brock falls head-over-heels for the attractive Professor Ivy and decides to stay with her, leaving Ash and Misty alone as a dynamic duo—at least until they meet intrepid Pokémon watcher Tracey
  • List of Episodes (36)
    • 26. The Pokémon Water War

      29 Jul '99
      On the next island, Ash and his friends see a team of firefighters consisting of Squirtles, Wartortles, and Blastoises. Eager to test its skills, Ash's Squirtle get to train with them. But when an actual fire turns up, training has to become reality.
    • 27. Pokémon Food Fight

      05 Aug '99
      While in a battle, Ash accidentally breaks Snorlax's Pokéball. With the Pokémon Center on the other side of the island, Ash and his friends have to get Snorlax there. And to make matters worse, Team Rocket arrive and are hoarding the island's food ransom until they get Pikachu.
    • 28. Pokémon Double Trouble

      12 Aug '99
      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.
    • 29. The Wacky Watcher

      19 Aug '99
      On Rind Island, Tracey meets Dr. Quackenpoker, a noted Pokémon Watcher who is doing a study on the Magikarp that climb up waterfalls and how they evolve into Gyarados. However, Team Rocket appears to steal the Magikarp and get them to evolve.
    • 30. The Stun Spore Detour

      26 Aug '99
      On Tiny Island, Ash and Tracey get affected by Stun Spore leaving it up to Misty to get an antidote to heal them. Can Misty find it with the help of her new Poliwag?
    • 31. Hello Pummelo

      02 Sep '99
      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.
    • 32. Enter the Dragonite

      09 Sep '99
      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.
    • 33. Viva Las Lapras

      16 Sep '99
      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 Tra
    • 34. The Underground Round Up

      23 Sep '99
      Having to travel by boat, Ash and his friends arrive on Hamlin Island, their final stop before returning to Kanto to discover that the town is being attacked by hundreds of Electrode. A man named Poncho is trying to stop them with his Diglett.
    • 35. A Tent Situation

      30 Sep '99
      They’re back in Pallet Town. When they get home, they discover Brock is back and he won’t explain why he left Valencia Island. However, as usual, Team Rocket try to steal all of the Pokémon in Oak’s lab by vacuuming all the Pokéballs, including the GS Ball that Oak was working on. Can they get it back?
    • 36. The Rivalry Revival

      07 Oct '99
      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 Oak's assistant. In the end, Brock rejoins the group and they head off to Johto.