Ruling Darkrai G

gengar the baller said:
If I put my opponent to sleep with Darkrai G which comes first the inbetween damage or the sleep roll?

"Put one damage counter on each of your opponent's Pokemon that remain Asleep between turns."

"... that remain Asleep..." That means that your opponent flips, and if they stay Asleep, you place one damage counter on them.
 
was going to answer but Kronar seems to have beat me to it, in addition though just in case you didn't already know you can also stack multiple darkrai G's so if you have 4 out thats 4 counters
 
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