Take a shot if the one monster you don't do well against is sweeping the tournament.
Take a shot when your monster learns a new attack.
Take a shot when, during battle, your monster hits an opponent with a powerful but inaccurate move.
Take a shot if your opponent hits you with a powerful, inaccurate move. Take another if they do it twice in a row.
Take a shot if a monster is knocked out in the first five seconds of a match.
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Down your drink in frustration if you were winning the entire match only for your opponent to win within the last 10 seconds.
Take a shot whenever a battle special is activated.
Finish your drink if your monster dies. You'll need it.
Take a shot every time something contains a translation error or grammatical error. If you have a liver of steel, do this for the Game Boy Battle Card game.
Alternatively, take a shot for every line of dialogue that is properly translated in the Game Boy Battle Card game.
In 4, take a shot whenever your opponent successfully counters one of your attacks, or you unsuccessfully counter an opponent's move. Take a shot in celebration if the opposite occurs.
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Anime
Take a shot whenever the Searchers call bad monsters "baddies" or good monsters "goodies."
Take another shot if the baddies call themselves baddies.
Take a shot when the heroes unlock a Mystery Disk.
Take a shot whenever a Monster becomes a Lost Disk. (Pro tip: Don't do this in Golem's debut episode, Tiger's debut episode, or when Monol relates the backstory of the world.)