One of the biggest parts of being a Pokémon Trainer is the ability to successfully utilize your Pokémon in battles against other trainers. While one can also battle against Pokémon, it is the Trainer Battles that really help show off a Trainer's skills, since Pokémon belonging to Trainers typically have stronger stats and more experience than wild Pokémon.

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On his journey to becoming a Pokémon Master, Ash had to win his way through several Pokémon Trainer battles against trainers, enemies, Gym Leaders, and random individuals as well. He made it a particular hobby of battling Team Rocket, but aside from their first encounter, their battles were not usually significant. He also battles several wild Pokémon, but these are considered unofficial battles since these often resulted in the acquiring of said Pokémon

10 Vs Jessie & James In "Ash Catches A Pokemon"

Jessie James Ash Pikachu Misty Pokemon

Ash's first Pokémon battle took place in Season 1, Episode 3, against classic Pokémon antagonist, Team Rocket. More specifically, members Jessie and James, became fan-favorite antagonists throughout the series' run, constantly going after Ash's Pikachu, as well as other Pokémon along the way. During the battle, Ash deployed both Pikachu and his newly-acquired Pidgeotto but failed to defeat Jessie's Ekans and James Koffing. It wasn't until he deployed his Caterpie that he turned the tables on Team Rocket.

9 Vs The Samurai In "Challenge Of The Samurai"

The Samurai Ash Pokemon

A classic Pokémon Trainer from the video games that players often encountered on the road between towns, Ash fought the Samurai in Season 1, Episode 4, while crossing through Viridian Forest with Misty. During that time, they come across a boy wearing samurai armor. Ash and the Samurai's battle mark's Ash's first official battle against another Trainer, although the battle ended in a stalemate, due in part to the Samurai recalling his Pokémon after noticing a swarm of Beedrill heading their way.

8 Vs Gym Leader Brock In "Showdown In Pewter City"

Brock Geodude Pikachu Pokemon

Originally a classic Generation 1 Gym Leader, the series made Brock famous for years to come due in part to the writer's choice to have him accompany Ash and Misty along their journey. In the anime, Ash battles Brock in Season 1, Episode, 4, during which he loses to Brock, the Pewter City Gym Leader. This was due in part to Ash's ignorance of Pokémon weaknesses and advantages. However, he returns the next day for a rematch in which he defeats Brock's Onix and Geodude. This episode also serves as the first time Ash's Pikachu uses the move, Thunderbolt.

7 Vs Gym Leader Misty In "Water Flowers Of Cerulean City"

Ash Butterfree Misty Pokemon

Fans of the original Pokémon games might've recognized Misty as the Gym Leader of Cerulean City, who had been traveling with Ash since Episode 2 of the series. But fans of the anime didn't learn about Misty's Gym Leader status until Season 1, Episode 7, when the gang travels to Cerulean City.

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After revealing she and her sisters are all Gym Leaders, Ash battles Misty for a Gym Badge, since all three of her sisters' Pokémon are too tired from previous trainer battles. Team Rocket, however, interrupts the battle just before Ash wins his battle against Misty.

6 Vs An Unnamed Trainer In "The Path To The Pokémon League"

Unnamed Trained Rattata Pokemon

At the very beginning of Season 1, Episode 8, Ash and Misty argue about Ash having two Gym Badges but very few Trainer Battles under his belt. This prompts Ash to find as many trainers as he can find, in order to raise his experience. The episode then cuts to Ash's Pidgeotto battling an unnamed trainer's Rattata. After the trainer's Rattata is defeated, Ash claims he's finally beaten 10 different trainers and boasts about how strong he is. The trainer then tells him he should check out an unofficial Pokémon Gym just down the road.

5 Vs Trainer A.J. In "The Path To The Pokémon League"

AJ Ash Pokemon

After battling the unnamed trainer, Ash, Misty, and Brock are told about an unofficial Pokémon Gym just down the road. After heading there they encounter Trainer A.J., who carries a whip and runs his own make-shift Pokémon Gym, where he challenges trainers to show off his strong skills. A.J. challenges Ash to a battle, where he summons a Sandshrew with his whip, while Ash chooses his Buterfree. AJ's Sandshrew defeats Butterfree and Pikachu, making it one of Ash's first lost Pokémon Trainer battles.

4 Vs Giselle In "The School Of Hard Knocks"

Giselle Ash Pikachu Pokemon

Ash's next official Pokémon win comes in Season 1, Episode 9, after encountering the Pokémon Technical Institute, a private school where Trainers learn about Pokémon battles, and whose students automatically qualify for the Pokémon League, without having to collect Gym Badges.  There, Ash battles the Technical Institutes' top student, Giselle, who boasted about being stronger than Ash after battling Misty. However, Ash's Pikachu (an Electric-Type) defeats Giselles Cubone (a Ground-Type), as Pikachu was more experienced than Cubone, despite being at a disadvantage.

3 Vs Gym Leader Lt. Surge In "Electric Shock Showdown"

Lt. Surge Ash Pikashu Brock Misty Pokemon

During Season 1, Episode 14, Ash and the gang arrive at Vermillion City after traveling on the road for two whole weeks. There, Ash battles Gym Leader LT. Surge, a tough Gym Leader who specializes in Electric-type Pokémon, including a rather intimidating Raichu.

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During their first battle, Lt. Surge is harsh on Ash and his Pikachu, making fun of its weakness, and saying he should evolve it if he plans on getting stronger. But during the rematch, Ash proves he doesn't need to evolve Pikachu to become stronger, as Pikachu is able to defeat Raichu using Quick Attack, a move Lt. Surge's Raichu had failed to acquire.

2 Vs The Gentleman In "Battle Aboard The St. Anne"

Ash Brock Misty Pikachu The Gentleman Pokemon

Throughout the Pokémon video game franchise, players often come across a Pokémon Trainer simply named The Gentleman. In Season 1, Episode 15, Ash battles The Gentleman while, aboard the cruise ship, the St. Anne, during a party hosted for trainers.  Ash battles The Gentleman's Raticate with his Butterfree and almost defeats the Raticate until The Gentleman calls back it, ending the battle in a draw. This eventually leads to the Gentleman asking Ash for a Pokémon Trade, between Butterfree and Raticate, to which Ash agrees, but later regrets.

1 Vs Team Rocket Grunts In "Battle Aboard The St. Anne"

Ash Pikachu Team Rocket Grunt Pokemon

While on the St. Anne, it is revealed that the party is actually hosted by Team Rocket, as part of a scheme to rob everyone of their Pokémon. During the robbery, Jessie and James command a group of Team Rockets Grunts, the first time the grunts appear in the anime. Ash, along with several other trainers, battle the Team Rocket Grunts in order to get everyone's Pokémon back. It was during this battle that Ash realizes he misses his Butterfree and chooses to stop what he's doing in order to search for the Gentleman to trade Raticate back for Butterfree.

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