Ashley is still fascinated by her victory and Winner's Trophy, while she and her Machop travel to the Goldenrod City and head to the Gym.
There, Ashley is dismayed to see a sign on the front declaring the Gym is closed today but will reopen tomorrow. With nothing else to do, the two decided to explore the city.
Ashley suggests visiting the Goldenrod Galleria, but gets the two of them lost. Machop then gets an idea about where to go and heads towards the main street. However, he runs straight into a Clefairy.
As Ashley apologizes to the Clefairy, a girl runs down the street, asking if Machop is okay and picking him up to kiss him on the head. He rubs the kiss off of his head.
The girl introduces herself as Whitney and offers to take the two to the Galleria, which she says is far easier to get to if they take an Underground Path that doubles as a shopping arcade.
As they are walking through the path, Whitney tells them that she discovered the route herself, and Ashley comments on how lucky they were to find her as a guide. However, Whitney winds up leading them further away from the Galleria.
Eventually, the group gives up on finding the Galleria and decides to head back to a hamburger stand they found earlier. Ashley thanks Whitney for her help, and Whitney tells her that she would love to have a battle against her.
Ashley thanks her but tells her that she is busy getting ready for a battle at the Gym the next day. At that moment, Whitney reveals herself as the Goldenrod Gym Leader, guides the two back to the Gym, and reopens it.
There, the referee announces that it will be a three-on-three battle, with a Plain Badge at stake. Whitney starts off with Nidorina, and Ashley responds by sending out Cyndaquil.
She had managed to catch the Johto starters, Cyndaquil, Totodile, and Chikorita that eventually evolved into a Bayleef.
Whitney orders a Poison Sting and a Tackle, but Cyndaquil counters with Flamethrower, eventually knocking Nidorina out. Whitney is shocked by the quick defeat and sends in Clefairy, who uses Metronome, but it winds up pulling out Splash.
Cyndaquil uses Flamethrower again, but Whitney cannot bear to see Clefairy get hurt and withdraws it from the match. Whitney then sends out a Miltank.
Ashley looks Miltank up on her Pokédex, which paints Miltank as a Pokémon who prefers not to battle. Whitney orders Miltank to use Rollout, and Miltank slams straight into Cyndaquil, sending it flying.
Ashley orders a Tackle and Cyndaquil attempts to hit Miltank but is unsuccessful. Miltank turns around and repeatedly strikes Cyndaquil until it is knocked out.
Ashley sends in her Machop. Whitney orders another Rollout, which heads straight for Machop. Ashley orders a Focus Blast, but it doesn't slow Miltank down and the Milk Cow Pokémon is rapidly approaching.
Ashley orders Machop to use Protect as a green barrier of energy appears around his body, protecting him from Miltank's Rollout, causing the Milk Cow Pokémon to fly upwards.
"Machop! Let's finish this with a Brick Break!" Ashley said as he lands a direct hit on the Milk Cow Pokémon's head with his Brick Break attack from above, knocking the Normal-type out in one blow and giving Ashley the victory.
Whitney admitted defeat since her Miltank lost and she is her toughest Pokémon in the whole world.
Whitney awards Ashley the Plain Badge, much to her surprise, she tells her that beating a Gym Leader's top Pokémon fair and square is what counts, as she accepts the diamond-shaped badge.