Take a Drink Whenever

Anyone says Pokemon

Anyone (including a pokemon) says the name of a pokemon
Double if a pokemon says a name of different pokemon

Alternate Game 1

Sip when:

Pikachu uses an electric attack

Ash whips out his Pokedex
Ash calls home to Professor Oak
The G.S. Ball is mentioned/seen
Team Rocket does their team motto
That Meowth Ballon appears
The Magicarp sub appears
James's Victreebell attacks him
Team Rocket goes "blasting off again."
Team Rocket uses their patented "dig a hole" trap
Officer Jenny appears
Nurce Joy appears
Brock hits on a girl
Brock's cooking
Misty mentions her bike
Misty gets all dreamy as she talks about something
Someone mentions a Pokemon Center
Psyduck appears
Wabbafett appears
Those words, "To Be Continued" appear