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It really depends. Random is random. Private and group giveaways are a bit easier. Don't get your hopes up too high on winning. That's my best advice.

Also; lergit.

You can do the math based on the average number of entries in the giveaways you've entered but I would expect to go at least 300-400 entries before you win.
Luck is fickle however, some have won several times in less then a hundred entries whereas there are a few with 600+ entries and no win.

As for your odds of receiving the gift if you actually do win, slightly less then 95% with the current stats on finished giveaways and I expect that ratio to be steadily increasing. With the gifter no longer receiving points it removes the incentive to create fake giveaways so their much less common then they once were.

You'll definitely have to be patient, you'll know you win as you'll get a yellow bar at the top of the site saying that you've won a giveaway and providing a link to the giveaway. Pretty much the same as appears when one of your giveaways finish.