Can I ask for a reroll if the winner won a game multiple times this month?

Yes.

Did Not Activate Previous Wins This Month

Because he did not activate his second copy, even if he wanted :3. Unless he already served his suspension, you'll be granted reroll without issues.

I did it like JustArchi said and it was approved. The guy in my case also made a giveaway out of the second win. Maybe you can check this too.

if the winner has at least one offense in the last month, you will get a reroll no matter if he was already suspended.

But why do you think they don't deserve your games? From what you're saying they didn't do anything wrong, they just were really lucky lately...

Thank you!!