Sometimes, Pokémon likes to throw a curveball at players by shoving a gym at them that is unfairly difficult. After coasting through the game, there is nothing more baffling than needing to barely scrape by with a win— or not being able to win at all. It makes sense for Gym Leaders to be more powerful than the other trainers around them in lore, but for the most part they just don't live up to it in game.
Whether it's the tasks required to get to them or the battles themselves, there are just some gyms that are infinitely more difficult than the others. It doesn't matter how many hours were put into level grinding or how much research has gone into type matchups.
10 Pokémon Sword & Shield's Dark Type Gym
Pokémon Sword and Shield introduced the Dynamax/Gigamax feature, something that nearly every gym in the entire region banks on for their signature Pokémon.
Not Piers. After fighting through an entire town which the madman has literally locked down, the player comes to find out that not only does Piers not like Dynamaxing his Pokémon, he has made it impossible to do so in his gym. To top it off, every single one of his dark type Pokémon have a counter for super-effective attacks, requiring both speed and power to get him down quickly.
9 Pokémon Sword & Shield's Fighting/Ghost Type Gym
With the Arena Challenge setup in Pokémon Sword and Shield it wasn't a surprise that some of the gyms had really intense challenges to get through. Depending on the version, players are met with either a fighting type or a ghost type gym in Stow-on-Side. While the battles themselves are pretty straightforward, the Gym Challenge itself isn't.
Players are put into a spinning teacup where they have to spin themselves through an arcade game. At the end of some alcoves there are either punching gloves or monster hands ready to snap the player into the opposite direction. Have too much trouble getting the spin to go just right? Have fun watching as the hands hit back more times than anyone cares to count.
8 Pokémon Gold, Silver, & Crystal's Normal Type Gym
So much time is spent pushing normal type Pokémon to the side as weak, primarily due to the fact they are effective against nothing. However, Whitney was the first to make players second-guess the type.
Whitney and her Miltank will go down in history as a harrowing duo. Given enough time, the cow can ramp up a rollout that has challengers begging for mercy. She made sure to let everyone know that with the right moves, any Pokémon can be a powerhouse and to not let a cutesy exterior fool them.
7 Pokémon Ruby, Sapphire, & Emerald's Psychic Type Gym
Mossdeep City set up their gym to throw one difficult curveball at challengers with the sibling duo of Tate and Liza. These two psychics force the player into a double battle, something that had only just been introduced in their generation. This means that players had yet to figure out how to really handle them by the time that these two showed up to show them the use of the battle style.
These two enhance their already powerful psychic types with moves that are beneficial to a double battle style making them a force to be reckoned with. They will go down in everyone's collective memory as that one gym nobody wanted to deal with.
6 Pokémon Red, Blue, & Yellow's Rock Type Gym
Brock himself is an icon of the Pokémon franchise, finding himself all over every form of media the company produces. He was the very first gym leader many players ever faced, drilling his way into the hearts of nostalgic fans everywhere.
Even though he was the very first leader, he was relentless. Two out of the four possible starting Pokémon a player could have chosen were weak against his rock types, and his Onix made sure they knew it. This wasn't even remedied until Charmander could have gotten Metal Claw in the remakes, and even then he would still thrash opponents without mercy.
5 Pokémon Sun/Ultra Sun & Moon/Ultra Moon's Water Type Trial
Instead of gyms in Pokémon Sun/Ultra Sun and Moon/Ultra Moon, players were met with trials. Different tasks had to be completed until the player would get to battle the totem Pokémon. The second trial the players had to face ended with a massively powerful Araquanid. By this point, few players really had much in the means to fight the water/bug.
It really didn't help that the field was constantly raining, with Araquanid having an ability to increase its stats while it did so. To top it off, it would call for other water/bug types constantly, leading for one infuriatingly difficult challenge.
4 Pokémon Ruby, Sapphire, & Emerald's Ice Type Gym
Wallace was definitely a character to stand on his own. He canonically won the Hoenn tournament and was rightfully the champion of the region; a title he took over in Pokémon Emerald. He also had his own contest series known as the Wallace Cup, which he would run while also keeping an eye on the eighth gym with his own mentor.
If that wasn't enough, his gym had to consist of massive floor cracking puzzles. Beat them all seamlessly and the player would be treated to only him as a battle. Fail, and the player would have to walk all the way through the basement and back through the puzzles to do it again. Then he makes matters even worse by focusing primarily on water types despite being the ice gym, effectively negating his primary weakness.
3 Pokémon Red, Blue, & Yellow's Psychic Type Gym
In the earliest games, psychic types were unfairly powerful in and of themselves. Until the second generation when dark type was released, the only type that was super effective against psychics were other psychics. The best chance a player had to have any real chance against her was either hitting her fast and hard, or hoping they could manage to catch an elusive Abra and get the thing to evolve at least once.
To top it off, many of her team were also ghost type, meaning any normal type attacks were ineffective. By all means Sabrina should have been higher in the league than she was at the time. Her power is greatly decreased in future generations, but it doesn't mean she can't still pack quite the punch. Not to mention every single one of the rooms in her gym made for a massive teleportation puzzle that got more confusing as it went on.
2 Pokémon X & Y's Fairy Type Gym
The Kalos region was the first of them to introduce the fairy type, and boy did Valerie make sure players understood their worth. For a region so rich in dragon types, she was a nightmare of a gym leader.
All of her Pokémon were sugary sweet and extra cute, leading for some opinions on how strong they rightfully should have been. She made sure that the new type had deeply ingrained itself into the series, showing off their phenomenal power in a devastating way.
1 Pokémon Gold, Silver, & Crystal's Final Gym
In Pokémon Gold, Silver, and Crystal, players are given the opportunity to go through the Kanto league after finishing the Johto. At the very end, players are met with the surprise of a lifetime when their rival in the previous game has taken over Giovanni's ground type gym. Then, instead of keeping up with the typing, he had kept the team of a champion instead.
So after fighting through an entire set of gym battles, destroying the Elite Four, and then running through all of Kanto's gyms, Blue shows up to remind players why he was once the champion himself. Granted he only had the title for a short period before Red stole it from him and ran away to the mountains, but the point stands.
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