It's always exciting when new Pokémon Trainers receives their first Pokémon, but for a girl named Dawn, things will be far more exciting than she'd ever imagined! Here in the Sinnoh region, Trainers receive their Pokémon from Professor Rowan, whose lab is near Sandgem Town—but soon after Dawn leaves her home in Twinleaf Town and heads for the lab, she's hopelessly lost. Fortunately, she runs into Professor Rowan on the street and follows him to the lab. But while the Professor was out, his assistants accidentally let two of the starter Pokémon, Chimchar and Pilplup, break out of the lab.

Dawn and Piplup begin their journey, and enter their first attempts to catch some Pokémon. Although, during those attempts, Dawn and Piplup run into Ash's Pikachu, and Team Rocket. Meanwhile, Ash continues looking for Pikachu and meets back up with Brock, and together they go catch up with Dawn.

While searching for Pikachu, Ash and Brock run into a new rival named Paul, who challenges Ash to a battle, but Ash can't compete without Pikachu; Dawn and Piplup meet Ash and Brock, and together they try to rescue Pikachu from Team Rocket.

"The journey of a thousand miles begins with a single step." This cannot be more true for Dawn as she now has Ash, a Trainer with many victories, 28 badges and a winner's trophy under his belt and Brock, the Pewter Gym Leader traveling with her now. As she is about to capture a Buneary, she makes mistakes which Ash points out and suddenly she smacks Ash with her Poké Ball. Soon they get into a big fight about it (Doesn't this sound familiar) and (as usual) Brock is in the middle of it. They soon notice the sun being extremely bright and find the cause: A Budew that belongs to a wandering minstrel named Nando, who just started his own journey. As a token of good will he offers Dawn a chance to battle him. How will she fair for her first battle and will she ever get along with Ash?

While heading to the first stop on their journey, Pikachu is captured by Team Rocket and Ash and co. are not far behind. After their balloon popped Team Rocket found Pikachu protected by a Turtwig. When Ash and co. find Pikachu with Turtwig its caretaker, a kindly old lady by the name of Clara, invited them over for lunch. Turns out she's a Pokémon Caretaker and Turtwig (like Bulbasaur before it) is her bodyguard but it really likes Ash. Will Ash accept Turtwig?

While en route to Jubilife City, Ash and co. encounter Paul again. He declares a Battle with Ash to see if Ash has gotten stronger since their last battle. Will this battle end differently for Ash, or will Paul have the advantage the second time around?

The roar of the crowd and the excitement in the air as Dawn prepares to start off her contest debut. Just kidding: it's just Dawn practicing (and failing) her appeals training. Elsewhere, Team Rocket stole some berries that belonged to a Golduck, Wooper, Quagsire and Poliwag. Soon after this group finds Piplup and it agrees to solve the problem. Can this plucky Pokémon settle this dispute diplomatically?

Still en route to Jubilife City, Ash and co. meet a girl named Minnie who tells the gang about a Gym called the Powerzone Gym. As usual Ash wants in on the Gym Battles so he, Dawn, Brock and Minnie check it out. What kind of Gym is this, and is it authorized by the Sinnoh League?

Early one morning, Ash is awoken by Dawn who is having a "Bad Hair Morning". And anyone who dares see her with bedhead will never see another sunrise again! After a Bubble Beam attack Dawn comes out with her hair silky smooth. Later Dawn spots a Buneary, a Pokémon she has tried so hard to capture, but this one seems to be infatuated by Ash's Pikachu. So she freezes everyone but Pikachu with an Ice Beam attack, but Pikachu did not like this and told her off, which broke her little heart. Can Pikachu be able to mend it, and will this Buneary be a part of Dawn's small Pokémon family?

Ash and co. finally arrive at Jubilife City, the first stop in Dawn's quest to be a great coordinator. It is there that she learns of a new fad. It's hip, it's hot, it's happenin' it's the Pokétch and, like all girls, Dawn has to have one. She gets one from three clowns only to find out from a smart little boy named Landis that it is a fake. Will she be able to get a real Pokétch, or will she be a trend loser?

The first of anything can be quite stressful. Dawn has made it to the Jubilife Contest hoping to win her very first ribbon. She meets a girl by the name of Zoey, who has a Glameow just like her mom. She also meet the fabulous Jessilina (Who unbeknownst to her is really Jessie). All eyes focus on newcomer Dawn. Will she have what it takes to make it to the top?

As the Jubilife contest continues, Ash, Dawn, Zoey and Jessilina (aka Jessie) pass with flying colors. But the tension mounds and pressure is really put on Dawn. Will she manage to win her very first contest, or will Zoey manage to win it all?

Ash and the gang find a Pokémon bird-watcher named Rosebay who wonders why the bird Pokémon have been recently disappearing. They decide to investigate at a nearby canyon where they spot Team Rocket capturing multiple bird Pokémon, including Ash's Starly. The gang works together to try and free the bird Pokémon, but will they be able to successfully save Starly from Team Rocket?

When Ash and his friends discover an injured and displaced Nuzleaf in a forest. Seeing that Nuzleaf is lost, they decided to return it to its home. Unfortunately, Team Rocket captures Nuzleaf and takes Brock along with he tries to stop them. However, Brock's quick thinking and culinary skills thwart their plans and helps Nuzleaf get home safe to its friends.

Ash, Dawn and Brock arrive at Oreburgh City, where Ash is stoked about getting his first Gym Badge. However, not only did Paul get there first but the Gym Leader isn't there. Apparently Roark, the Gym Leader, went to the mines to dig for coal. When they run to meet him he said that he totally forgot his duties as a Gym Leader. When they go back, Roark decides to challenge Paul first. Will Paul be able to beat Roark?

After Paul dominated the Oreburgh Gym, Ash had to think about what Pokémon he could use. Naturally he chose Turtwig, Aipom and Pikachu to go up against Roark's Rock-type Pokémon. Will this strategy work, or will history for Ash repeat itself?

After Ash suffered a defeat last time, he doesn't let it bother him as he trains with his Pokémon for his rematch with Roark. Meanwhile, Team Rocket resurrects an Aerodactyl that goes nuts and nearly destroys the city. Can Ash be able to face this ancient Pokémon again? And will Dawn be ready for her next contest?

Ash returns to Oreburgh Gym, ready to challenge Roark again. As the battle starts, Ash quickly surprises everyone when Pikachu manages to take down Onix. As the second battle begins, Ash pits Aipom against Geodude. After a long struggle, Ash manages to beat Geodude, and loses Pikachu and Aipom before the real test begins, defeating Roark's newly evolved Rampardos.

Dawn catches a Pachirisu but quickly discovers the cute Pokémon may be too feisty to control. Seeing this, Dawn questions her competence as a trainer. Meanwhile, Team Rocket also wants Pachirisu as they try to lure it with food in order to capture it.

On the way to Floaroma Town, Ash and the others hear some screaming nearby. At a house, a Pokémon hunter named J has just captured a girl named Melodi and kidnapped her Gardevoir and she quickly flees the scene. Ash gives chase to her, and tries to battle her, only to have Pikachu frozen in stone and stolen just like Gardevoir. They decide to help Officer Jenny and try to help capture J, but eventually she also gets Meowth as well! Before she can take off, Ash, Jessie, and James sneak under her vehicle and follow her to her secret flying base. Now, the reluctant allies must work together to get back their Pokémon from J's clutches.

While they were walking tiredly, Team Rocket once again encounter the Magikarp salesman, not having forgotten how he tricked James into buy several Magikarp. James tries to take his money back until Magikarp salesman convinces Team Rocket to buy an Evolution Machine. Meanwhile, Ash and co. visit Oralie and Haley, two coordinators that claim to have the strongest Magikarp and Feebas ever. After both Ash and Dawn's defeat by Oralie's Magikarp, Team Rocket steals Magikarp, Feebas and Pikachu and tries to evolve them. Will they succeed?

Aipom takes Ash's hat and playfully runs away, but then finds itself in trouble. However, Aipom is saved by Jessie and then convinces Ash to let her use his Pokémon in an upcoming contest. Although, Ash worries that he may lose his Aipom to Team Rocket.

When Team Rocket was planning their next pitfall trap, their shovels suddenly got stuck in the ground. When they try to pull them out, a Steelix pops out of the ground with the shovels stuck in its head. It grows angry and begins to chase them. Meanwhile, Ash and his friends discover an injured Bidoof. After healing its injuries, they decide to help it go back to its village. However, Team Rocket and the rampaging Steelix come by, forcing them to run into Bidoof's Village. Lucky for them, the Bidoof Village is surrounded by a huge rock wall, but Steelix will be able to break through. Now Ash and the others must find a way to stop Steelix before it destroys the Bidoof Village.

When a girl named Theresa asks Ash to let Pikachu stand in for her aunt Abigail's lost Pikachu, Sugar, to help her win a baking competition, the ruse seems to work, until Abigail challenges Ash to a Pokémon battle against Pikachu. Will Ash be able to battle his own partner and best friend.

Arriving in Floaroma Town, Dawn drags Ash and Brock to a cooking class to learn how to make a special Pokémon snack food called poffins. Meanwhile, Team Rocket hatches a scheme to get rich selling their own poffins, but a shy Roserade upends their plans.