Pokémon: The 10 Orange Islands Pokémon Battles, Ranked

This archipelago put Ash’s skills to the test, and there were some amazing battles to be found in and even outside of the gym battles in Pokémon.

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Throughout Pokémon anime, Ash has gone to some interesting places on his journey to be a Pokémon Master, but one of the more unique legs of his quest had to be when he visited the Orange Islands. While not an official region of the Pokémon world, it did have its own Pokémon League and was home to some pretty skilled trainers.

The Orange League played out a little differently than other regions usually do. This archipelago put Ash’s skills to the test, and there were some amazing battles to be found in and even outside of the gym battles.

10 Ash VS Danny

As previously mentioned, the Orange League took a different approach to battling. In fact, some of the battles weren’t even battles but tests of skill, such as the case with this Orange League Gym Leader, Danny. Danny put Ash through quite the trial, having him climb a mountain without the aid of his Pokémon, make a toboggan out of ice and then race him down the mountain in the said toboggan.

Danny’s trial is focused more on a trainer working with their Pokémon rather than barking orders. Fortunately, Ash can do this ultimately overcomes the challenge. This Gym Leader’s challenge was head-scratching in some respects, but the lesson is definitely there.

9 Ash VS Cissy

Like Danny, Ash’s match with the Gym Leader Cissy was more based on special challenges than a traditional battle. Cissy would have Ash go toe-to-toe with her Seadra in a battle of marksmanship with the move Water Gun and then pit his Lapras against her Blastoise in an ocean race.

While Danny’s match was solely dependent on a trainer working alongside their Pokémon, Cissy’s challenge was more based on skill and instinct. As such, Ash ended up improvising in an unfamiliar situation and creating a strategy on the fly that won him his first Orange League badge.

8 Mateo VS The Crystal Onix

Ash wasn’t the only one getting into some unique battles in the Orange Islands. Some of his companions (even short-lived, “character of the day” ones) got a shot at it too. In the case of this battle, the glass craftsman Mateo got to battle a Crystal Onix, a precursor to Shiny Pokémon, to cure his artist block.

The Crystal Onix itself seemed to be completely different from others, being able to resist water-type moves entirely, which forced Mateo to battle it with his Charmeleon after his Cloyster gets knocked out. While the battle itself ends up having no winner, Mateo does understand this one of a kind Pokémon and finds the inspiration he was looking for.

7 Ash VS Gary

After their rivalry raged across the Kanto Region, Ash finally got a chance to battle Gary after returning victorious from the Orange League. Getting something of a swelled head after his triumph, Ash thinks he’s got this one in the bag, but reality hits him pretty hard when Pikachu gets defeated by Gary’s Eevee.

With his confidence taken down a notch, Ash is inspired to push even further and become stronger, which leads him to his eventual decision to take on the Johto League, where he’d have his epic rematch with Gary.

6 Ash VS Prima/Lorelei

Ash doesn’t meet the Elite Four members all too often, but when he does, he usually learns why they’re such respected trainers. While traveling the archipelago, Ash runs into Lorelei (her name changed to “Prima” in the anime), who had a lesson in humility in store for an over-confident Ash.

Showing wit and flawless strategy, Prima ends up having her Cloyster tank hits from Pikachu, who definitely had the advantage, and won the battle with a well-placed combo move. Ash had a valuable lesson to learn from all this, while Prima proved why she’s an Elite Four member.

5 Ash VS Rudy

Ash’s third Orange Island badge came from challenging a Gym Leader who had a thing for Misty, Rudy. At first glance, Rudy’s challenge took a page out of Cissy’s book, but he took things a step further. Rudy had Ash first pass a target test while on a moving boat and later had a real battle in a three-on-three “same type” match up.

Ash’s battle with Rudy put his Pokémon up against some pretty tough opponents, but through perseverance, Ash was able to pull through and even got his Squirtle to learn “Hydro Pump” during it, which won him the match.

4 Ash VS Tad

While Tad may not have been an Orange Island Gym Leader, he and his Poliwrath were still pretty tough opponents for Ash. In the first round, Tad’s Poliwrath easily took Pikachu and then Charizard right after, a victory that even Tad thought was too easy.

It was only by staying by Charizard’s side while nursing him back to health that Charizard finally began to listen to Ash, and with their bond strengthened, Ash was able to give Tad a rematch, and Charizard won the day with one good Seismic Toss.

3 Misty VS Marina

Misty doesn’t always get to have a big head-to-head battle with anyone, let alone a trainer with love for water-types like her. Fortunately, Ash’s Orange Islands adventures didn’t keep Misty completely on the sidelines, as she got into a pretty amazing battle with the water-type trainer, Marina.

It’s a pretty intense battle that really had Misty on the ropes for most of it, and it was only after using Golduck (which she believed at the time was her dopey Psyduck evolved) that things turned around. While that Golduck wasn’t technically hers, she did manage to prove her skill as a trainer with the wild Pokémon.

2 Ash VS Luana

Luana was one of the only Orange Island Gym Leaders who had something of a straightforward challenge for Ash and one of the first to adopt the idea of “Double Battles” before they became official. Luana didn’t hold anything back either, sending out her strong Alakazam and Marowak against Ash’s Pikachu and Charizard.

While things didn’t start so smoothly for Ash, Pikachu and Charizard managed to start fighting each other instead of Luana’s Pokémon, the two did settle their beef and managed to pull off some good combo moves that won Ash his final Orange Island badge.

1 Ash VS Drake

Hands down, Ash’s greatest battle during the entire Orange Islands saga of his journey was against the Orange League’s “Supreme Gym Leader,” Drake. Drake’s diverse team of Pokémon really put Ash through his paces and made him think more strategically for each matchup, making for an equally epic and intense battle.

Drake really had Ash in a corner for a while there, especially when his Dragonite was able to defeat Ash’s Charizard, but through quick thinking and fiery spirit, Ash was able to win. Some may not consider the Orange League as an official Pokémon League, but it was still Ash’s first major victory, and nothing can take that away from him.

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