S02

Pokémon: Adventures in the Orange Islands (originally branded on Kids' WB! as Pokémon: Orange Island Adventures) is the second season of the Pokémon anime. This season showcases the adventures of, , and in the Orange Islands before they return to Pallet Town. The subtitle "Adventures in the Orange Islands" is not used within the broadcast episodes, but was later added by the DVD boxed sets to distinguish it from the later seasons.

It originally aired as part of the 1999-2000 Saturday morning line-up. The season began with Princess vs. Princess, which originally aired on September 4, 1999, and ended with Charizard Chills, which originally aired on September 2, 2000. It was preceded by Pokémon: Indigo League and succeeded by Pokémon: The Johto Journeys.

Blurb
''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 Sketchit!''

Important events

 * journeys to Indigo Plateau to compete in his first Pokémon League Conference.
 * The Indigo Plateau Conference takes place. (EP074 - EP080)
 * loses to Melissa in the fourth round, placing him in the Top 32. (EP077)
 * Ash loses to Ritchie in the fifth round, finishing in the Top 16. (EP079)
 * Ritchie loses to Assunta in the sixth round and is placed Top 8. (EP080)
 * tells Ash to journey to the Orange Archipelago to pick up the mysterious GS Ball, which cannot be teleported via PC. (EP081)
 * Ash meets Professor Ivy and retrieves the GS Ball from her lab. (EP083)
 * stays behind with Professor Ivy and becomes her assistant. (EP083)
 * Ash and meet, a Pokémon watcher who joins the group. (EP084)
 * Ash decides to challenge the Orange League. (EP084)
 * Ash's Charizard finally begins to listen to him. (EP105)

Additions
The following Pokémon are obtained:
 * Jessie's Lickitung (EP052)
 * Jessie's Shellder (EP066)
 * Ash's Lapras (EP084)
 * Ash's Snorlax (EP094)
 * Tracey's Scyther (EP097)

Evolutions
The following Pokémon evolve:
 * Ash's →  (EP075)
 * Ash's →  (EP081)

Releases
The following Pokémon are released:
 * Jessie's Shellder (EP066)
 * Ash's Pidgeot (EP081)

Other

 * Misty's Horsea (left at Cerulean Gym, EP061)
 * Misty's Starmie (left at Cerulean Gym, EP061)
 * Tracey's Venonat (obtained prior to EP084)
 * Tracey's Marill (obtained prior to EP087)

Gym battles
Ash defeats the following Gym Leaders:
 * Blaine, after one failed attempt (EP059)
 * (substituting for ) (EP063)
 * Cissy (EP085)
 * Danny (EP093)
 * Rudy (EP103)

Trivia

 * Many clips of 's adventures in the Orange Archipelago were first shown in via Pikachu's Jukebox.
 * This season has the longest name, totaling at 28 letters.
 * In, the Orange Archipelago arc was completely skipped.
 * This was the last season of the to air in  before it went on a hiatus that wouldn't be broken until the  was dubbed and aired seven years later.
 * Due to using the TV definition of Pokémon: Indigo League and the home video definition of Pokémon: The Johto Journeys, it includes episodes from both definitions, from Princess vs. Princess to The Rivalry Revival, as the second season.
 * This season was originally branded on Kids' WB! as Pokémon: Orange Island Adventures.
 * Older home video releases refer to the season as "Pokémon: Adventures On The Orange Islands" (in the United States) or "Pokémon: Adventures on the Orange Islands" (in Australia). Newer DVD releases refer to the season as "Pokémon: Adventures in the Orange Islands".
 * On Pokémon.com, the logo reads "Pokémon: Adventures In Orange Islands 1". This logo is likely derived from the cover of the US DVD release Pokémon: Adventures On The Orange Islands 1.