Multiple wins and non-activated wins??

Yes you can ask for a re-roll in these cases, but a re-roll will only be granted if the user doesn't have served a suspensions for the infraction, yet. Independently, it will always be granted if the infraction occurred during the past month.

These are the two rules you base your request on:

Entering

Only enter to win games you do not already own, and do not enter to win DLC if you're missing the required base game.

Winning

Won gifts should be activated to the Steam account used during registration, and they should not be regifted, traded, or sold.