how many here have actually won something?

I probably would have one a lot of games, by now, but this guy named Anonymous keeps beating me out in every giveaway I enter.

I don't think he's really legit, though.... I can't view his profile, and he keeps losing his prize to someone else when they re-roll.

To be a bit more serious, most people on the site win about as many games as their estimated win total. Since the drawings are random, like the lottery, there is no guarantee that you will ever win anything at all. Ever. Even so, the majority of people on SG seem to win their first giveaway before 2000 entries. Your mileage will vary, but you can increase your chances by entering giveaways where there are fewer entrants.

got skyrim

I won a hotdog eating contest and got 500 dollars

In 9 months you've only entered 55 giveaways. Probably all publics with many hundreds of entries. The fact you haven't won (if that's what you're alluding to) isn't exactly mindboggling.