Can i create an underdog giveaway?

You can make a giveaway with special rules like letting only people with 0 wins enter, but it must be private and approved by support.

You can make a private giveaway for that purpose after getting special rule approved by support :)

Either a private giveaway with the special requirement approved by mods, or a group giveaway with said special rule.

You can not have special requirements for a public giveaway.

Oh ok i see, thank you for the replies.

The community calls that kind of giveaway a "Cherry Popper" giveaway.

1) Make a Support ticket asking if you can make a private giveaway with the rule that requires entrants to have no wins from SteamGifts.
2) After getting approval, make a private giveaway and post the rule clearly in the description.
3) After the giveaway is up, make a posting in the forum giving the rule(s) of your giveaway and a link leading to it.