Japanese Title: Rival Showdown! Satoshi VS Shigeru!!
Original Airdate: October 7th, 1999
US Airdate: October 14th, 2000
An errand of Professor Oak's sets Ash on the road once again, but first he must face his old hometown rival, Gary, in a Pokémon battle.
- And the Adventure Continues: The segue into the Johto league adventures.
- Ascended Fanboy: Tracey has been taken under Professor Oak's wing.
- Break the Haughty: Ash is proud of his victories in the Indigo and Orange Leagues, but is still beaten by Gary. Gary points out that the first was a long time ago, and he's been training too while Ash was in the Orange Islands.
- Character Development: Gary no longer has his fawning cheerleaders.
- Diagonal Cut: Scyther chops Team Rocket's fake camera in two...without harming Picachu inside it.
- Dramatic Wind: One blows through Professor Oak's study when he mentions New Bark Town, "Town where winds of new beginnings blow!"
- Epic Fail: Gary totally ignores Team Rocket's slogan presentation.