Gen 1
Gen 2
Gen 3
Gen 4
Who's That Pokemon?
100

You are unable to get through Rock Tunnel without this move.

What is Flash?

100

This is the place where you first encounter Entei, Raikou, and Suicuine.

What is the Burned Tower?

100

This area became available during the post game where you are able to compete in different types of battles with many variations.

What is the Battle Frontier?

100

This Pokemon was able to evolve by leveling it up around two certain types of rocks.

What is Eevee?

100

It is born with the ability to defy gravity. It floats in air on powerful electromagnetic waves. (Gen 1)

What is Magnemite?

200

What item do you get after defeating 5 trainers and a Team Rocket member at the end of the bridge north of Cerulean City?

What is a nugget?

200

You find this person atop Mt. Silver when you collect all 16 Gym Badges.

Who is Red?

200

What does your father give Wally in order to catch his first Pokemon?

What is a Zigzagoon?

200

What does your rival threaten to do to you whenever you are late to something?

What is fine you?

200

It wraps things with its extensible tongue. Getting too close to it will leave you soaked with drool. (Gen 4) 

What is Lickilicky?

300

When you visit this place in Pokemon Gold and Silver, it was destroyed by a volcano.

What is Cinnibar Island?

300

This niche accessory was sold with Heard Gold and Soul Silver.

What is the PokeWalker?

300

At the release of this game, this Pokemon had no weaknesses.

What is Sableye?

300

What item did Cyrus use to try and control Dialga and Palkia?

What is the Red Chain?

300

Their wings have not yet completed the process of growing. Rather than flying long distances, they are more useful for generating ultrasonic waves by vibrating. (Gen 3)

What is Vibrava?

400

In the Japanese release of the original Pokemon Green, what real world health issue did many children suffer from when visiting a certain town.

What is Lavander Town Syndrome?

400

These types of evolutions were introduced in this generation.

What are baby Pokemon?

400

This type of battling was first introduced in this generation.

What are Double Battles?

400

This Pokemon was only able to be obtained by breeding another Pokemon that had to be transferred from Pokemon Ranger.

What is Phione?

400

To shelter itself from cold, wintry winds, it covers itself with a cloak made of twigs and leaves. (Gen 4)

What is Burmy?

500

Amnesia was regarded the strongest move in the game for this reason.

What is sharply raising Special stat which was not split into attack and defense?

500

Many players were happy with this very small addition added to player customization in Pokemon Crystal.

What is the ability to play as a female?

500
What was the item created to help you catch Pokemon in the Safari Zone?

What are PokeBlocks?

500

This was a revolutionary change to all moves used in this generation.

What is the Physical/Special Move Split.

500

Because the long hair all over its body obscures its sight, it just keeps charging repeatedly. (Gen 2)

What is Piloswine?