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A trainer checking his pokégear

Important dates mentioned on this site

When the games were released

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Contents:

1998 (Pokémon Red & Blue)
1999 (Pokémon Yellow)
2000 (Pokémon Stadium)
2000 (Pokémon Gold and Silver)
2001 (Pokémon Crystal & Stadium 2)
2003 (Pokémon Ruby & Sapphire)
2004 (Pokémon Colosseum)

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1998

The first Pokémon games released, Pokémon Red and Blue, were games in which trainers from Pallet Town received a starting pokémon (either Bulbasaur, Charmander, or Squirtle) and explored Kanto, fighting its gym leaders, to reach the Pokémon League in Indigo Plateau and beat the Elite Four. There were about 150 known pokémon then.

1999

Pokémon Yellow, released a year later, was just about the same as Pokémon Red and blue, only that players sort-of followed Ash Ketchum's TV story since they started with a Pikachu and got the other three starters in the same way Ash did.

2000

The Pokémon Stadium took pokémon trainers to a 3D town where they battled other trainers in stadiums.

2000

In Pokémon Gold and Silver trainers from New Bark Town received either Chikorita, Cyndaquil, or Totodile as a starting pokémon. They explored Johto with the help of the pokégear and battled the Johto Gym Leaders. About 250 pokémon were known by then.

2001

Pokémon Crystal was pretty much the same as Gold and Silver; the main difference was that players could pick their gender before beginning. There was also a few additional hidden goodies in places like the Ruins of Alph for those who dared to explore further.
In the same year, Pokémon Stadium 2 was released. Not only did it allow the players to battle other trainers in the stadiums like its antecessor of the previous year, but it also included a greater amount of information and fun within it!
The above image is larger than it may appear.

2003

The games for Gameboy Advance took a longer while to come out, but finally, in 2003, Pokémon Ruby and Sapphire were released in full.

These games let trainers who just moved into Hoenn explore this new region where there was about one-hundred new pokémon. The starting pokémon they could choose were Treeko, Torchic, and Mudkip. They could beat all the gym leaders and then the Elite Four in Evergrande City and participate in Pokémon Contests as well.

2004

The Pokémon Colosseum, though it didn't present any pokémon unknown by then, took place in Orre, an entirely 3D region. This game also presented the concept of snagging and purifying Shadow Pokémon. Its Battle Mode allows players battle other trainers in several stages, just like in the Pokémon Stadiums mentioned above.

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