In this article, we will explore the toughest battles in the entire Pokemon series. This will give you an idea of how to prep for them.

In Pokemon games, the toughest battles are the ones that you need to put a bit of effort into and aren’t guaranteed a win. While the Elite Four and Champions of each game are known to be difficult, they can usually be prepared for. However, for the trainers on this list, you either don’t have the best options available when facing them, or even with your best possible team, as they are just too powerful. So let’s take a look at the toughest trainers in the mainline Pokemon games.
The Toughest Battles in the Pokemon Mainline Games
Here is a ranking of the most difficult battles in the mainline Pokemon games, from easiest to hardest.
- Whitney (Gold/Silver/Crystal/HeartGold/Soulsilver)
- Norman (Ruby/Sapphire)
- Ghetsis (Black/White)
- Elesa (Black/White)
- Cynthia (Diamond/Pearl/Platinum/BrilliantDiamond/ShiningPearl)
5. Whitney (Gold/Silver/Crystal/HeartGold/Soulsilver)

Being beaten by Whitney is a rite of passage for a Pokemon trainer. Her main threat is from her Miltank, which at this point in the game outspeeds everything. This becomes an issue as that cow can flinch you with Stomp, heal itself with Milk Drink, or immobilize with the power of love with Attract. All before your Pokemon has a chance to move. Not to mention using Rollout to accumulate damage quickly with each turn.
Now, while Whitney is on this list and her Pokemon battle is unquestionably tough, there is a counter provided for the player. In Goldenrod City, where Whitney’s Gym is located, you can trade a Drowzee for a female Machop. This Machop will be immune to Attract from Whitney’s Miltank, and thanks to being a Fighting-type, it resists Rollout and hits Miltank for super effective damage. It can still be flinched with Stomp, though.
4. Norman (Ruby/Sapphire)

While he loses his edge a bit in Emerald and the Gen 6 remakes, in Ruby and Sapphire, Norman is at his deadliest. Yes, his two Slakings can’t attack consecutively, but when they do, very few Pokemon at this point in the game resist their attacks. Using status conditions like Poison or Paralysis will not help, as it boosts the power of their STAB Facade from 70 base power to 140 base power. Both of his Slakings and his Vigoroth have Faint Attack to hit the usually immune Ghosts as well. The best way is to use Protect to stall out the turns of his Slaking’s attack, with Dustox and Pelipper learning the move through level up.
3. Ghetsis (Black/White)

The final boss of Pokemon Black and White, Ghetsis, more than deserves his reputation. While his team is reasonably diverse, what put him on this list was his ace Hydreigon. With a movepool of Dragon Pulse, Surf, Fire Blast, and Focus Blast, this pseudo-Legendary hits everything in the Pokedex for powerful neutral damage. While Ghetsis’ team has its flaws; for instance three of his Pokemon are weak to Fighting-type attacks, those flaws don’t seem to matter as much while battling him.
2. Elesa (Black/White)

If you are wondering how a Gym Leader from Black and White provides a tougher Pokemon Battle than the final boss, you need to rebattle her to find that out. Elesa is the fourth Gym Leader specializing in Electric-types. Except two of her Pokemon are Emolga, which are part Flying and immune to Ground-types. And all of her Pokemon have access to the switch move Volt Switch, which lets them switch around in battle, a rare occurrence in-game.
What put her so high on the list is the lack of options you have for dealing with her at this point in the game. All three starters are weak to her Emolga. Two of the Elemental monkeys, Simisage and Simipour, are weak against her team. None of the usable Ground-types learn Rock-type moves at this point, unless you overlevel your Drilbur for Rock Slide and have to rely on the Rock Tomb TM. Meanwhile, the Rock-types at this point have low special defense and cannot last against constant Volt Switch spam. Expect a lot of switching, healing, and losing turns to paralysis (both her Emolga have the ability Static) while facing off against her.
1. Cynthia (Diamond/Pearl/Platinum/BrilliantDiamond/ShiningPearl)

To nobody’s surprise, Cynthia remains the queen of tough Pokemon battles. In any Sinnoh game you face her, she is guaranteed to give you a workout. And she isn’t limited to Sinnoh either, with her making a surprise appearance in Black and White as well. While each of her Pokemon is tough, it’s her Garchomp that will give you the most trouble thanks to its speed and raw power. Even a full team of six at the end of the game, with all the options you would want, may not be enough to defeat Cynthia.

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