Let’s start with this guy, who appeared in the Diamond & Pearl series. Barry is from the Sinnoh region, which was inspired by Hokkaido and parts of Russia that are close to Japan. Barry is a hyperactive Pokemon trainer who dreams of being as good as Paul. Although he favours strength in his critters, Barry truly cares for them.

Barry’s rivalry with Ash started when Ash was going to challenge Fantina, the owner of the Gym of the local town. At first, Barry thought Ash’s methods were not good, but our protagonist beat him. Once Barry saw Ash fighting against Fantina, he recognized he was excellent, so a friendly rivalry was born. We see Barry several times during Ash’s and company travel in the Sinnoh region.

This was an interesting female triple rivalry that was featured in the Diamond & Pearl series. The battles of these three ladies were focused on their abilities as Pokemon Coordinators (feeding Pokemon special diets and teaching them moves to look at their best). Dawn always dreamed of becoming a Coordinator, just as her mother. As for Ursula, she has a very similar level to Dawn when they meet, which prompts her antipathy for her.

And Jessilina… well, she is Team Rocket’s Jessie’s alterego. This is notable because Jessy borrowed a Pokemon from Ash (Aipom), and even won against Dawn! The skills of Jessie as a coordinator were shown off frequently on the series, advancing to the semifinals of the Sinnoh Grand Festival. In the end, none of the three girls won the first place, but won a lot in experience and even ended admiring each other a little bit.

Apparently, the Diamond & Pearl Pokemon series gave us several interesting rivalries, right? Let’s meet Paul, who was the main nemesis for Ash in this series. He is, for the lack of a better word, a bully. Paul scolds his Pokemon and trains them to the point of exhaustion. So, we can see how he is obsessed with strength.

Everyone assumes Paul is a full Pokemon trainer, but it turns out that, although he has participated in several conferences, the guy has not won in one yet. Of course that, being such a strict Pokemon trainer, he clashes with Ash’s method of bonding with the little critters. Paul accuses his rival’s Pokemon to be weak with the possible exception of Pikachu. Thus, Ash doesn’t win Paul’s respect until he defeats him on the Lily of the Valley Conference.

For a long time, we saw Jessie, James and Meowth from the Team Rocket battling single handedly to do evil deeds in the Pokemon world. But Team Rocket is huge, my dear Pokemon trainers! Rivalries also thrive inside its lines. We can see that Butch and Cassidy are an interesting contrast for Jessie and James.

Although the two girls are kinda vain, Cassidy is more controlled and even manipulative, as she enjoys driving Jessie mad. As for Butch, he is more like a comedic relief, always correcting other characters when they pronounce his name wrong. Nevertheless, Butch and Cassidy are more brainy and subtle than Jessie and James when they steal Pokemon. These two themes of bad guys are supposed to be on a race to catch a red colored Snorlax, but so far, none of them have been successful.

We simply couldn’t leave this old rivalry out of the count, as the most recognizable members of Team Rocket are a recurring gag in the anime. But as the series progresses, we find out more about the ones who are always trying to steal Pikachu or doing evil stuff around Ash and his friends. Jessie was the daughter of a Team Rocket agent herself, but when her mother disappeared in Los Andes, she was sent to an orphanage. This girl also tried to become a Pokemon Nurse, but was so poor that she only could be accepted in a Nursing School for Chanseys. After that, she enrolled in a Pokemon Technical School where she met James, who became her partner in crime.

As for James, he was raised in a rich family who paid all sorts of extra lessons for him. But the lifestyle was unbearable to James, and when his family engaged him to a certain controlling lady named Jessebelle, he ran away. Next, James enrolled into the Pokemon Tech, where he met Jessie. They eventually joined Team Rocket, where they have been trying to succeed in the missions commanded by their boss since the very first episode of the series. The abilities of these two with Pokemon have evolved considerably, although they still fail at becoming evil guys. But hey, they are there to give us something to laugh about, right?

This curious Pokemon rivalry was shown in the Best Wishes series. Iris is an aspiring Dragon Master from the Unova region who was Ash’s travelling companion for a while. She got Dragonite when he crashed into a power plant due to an injury. Iris was so keen to defend his innocence in the incident that the Dragonite decided to join her in the journey!

Everything was cool for a while, until a Kanto themed fair visited Unova. When Ash met Professor Oak there, he remembered his Charizard, who was training at the Charicific Valley with other Charizards. So, Professor Oak brought Charizard back through trade, and guess who had immediate antipathy for him? The Dragonite! So, Ash decided they could have a fight… which ended up being a wise decision. The fight was intense and both Pokemon learned to respect each other.

Let’s continue with Trip, who appears in the Best Wishes series. The setting is the area of Unova, which is inspired in New York City. Hum, maybe that’s why Trip is blond? Anyway, this guy dreamed about becoming a Pokemon trainer since he met the experimented Alder, champion of the Unova region.

When Ash arrives at Unova, bad luck stroke him… Well, not him, but Pikachu, in the form of a thunderstorm that wiped away his powers for a time. That was just when they meet Trip, who is eager to battle Pikachu, as he is not a usual Pokemon in Unova. But once poor Pikachu is defeated by Trip’s Snivy, Trip leaves with the impression that the Kanto area is somewhat inferior. Here we see how prejudice can foster rivalries (tut, tut). Trip would persist on this view for a long time, although Ash proves again and again that he can handle his Pokemon, and even trains his own Snivy. But well, Trip finally becomes a friendly rival for him at the Vertress Conference, when Ash’s Pikachu defeats Trip’s Serperior.

This guy had such a successful appearance in the Mega Evolution Special, that he managed to also show up in the XY series. Alain and his mentor, Professor Sycamore, are from the region of Kalos, which is based in France. He has concentrated in finding Mega stones to trigger Mega evolutions in Pokemon. So, we can seehe is a serious rival for Ash.

Alain was intrigued by the power of Ash’s Greninja, so they had a battle. Although Ash lost, they had other battles before both entered the Lumiose conference. In contrast with other Conferences, Ash reached the finals, only losing to Alain. The battle between Mega Charizard X and Greninja was one of the best in the Pokemon series. Plus, this is a non bitter rivalry. Both guys are interested in their Pokemons and are clean competitors 🙂

We just had to rank this nostalgic rivalry in a high place. Afterall, Red and Blue are the very first Pokemon Trainees that ever existed. Their story was fleshed out in the Pokemon Origins short series, set in the Kanto area. Anyway, Blue is Professor Oak’s grandson, while Red is an enthusiastic guy who dreams of becoming a Pokemon Trainer. Red is also shown to be clumsy and at first does not catch up with the idea that Pokemon are friends are not tools. As for Blue, he is self centered and very competitive towards Red.

Their rivalry is not only driven by their wishes to become Pokemon masters. Professor Oak also entrusted them with the mission of collecting information on all the Pokemon in the Kanto area. Although this pair is very similar to that of Ash and Gary, they are more mature from the start. And those epic battles that culminated with Red victory in the Kanto League! They definitely get extra points for all the nostalgia.

And finally, the ultimate Pokemon rivalry has to be Ash vs. Gary. Not only because it was the very first one depicted in the series, but also because it was the one that developed best. Gary is Professor Oak’s grandson, and since the first time we meet him, it is noted that he is a jerk. He has fangirls, money, and talent. Poor Ash just starts with a rebellious Pikachu and not much luck.

One time, it is revealed that Ash and Gary used to be friends until they both caught a Pokeball while fishing in Palette Town’s river. Because Gary considers that half a victory against Ash is still a defeat, his pride is injured. Although he was not directly defeated by Ash in the Pokemon League, he eventually learned to acknowledge him as a Pokemon Trainer. Their friendship was restored and Gary has done several sporadic appearances in later series since then, travelling the world as a Pokemon researcher.