Indie Gala 4

The Binding of Isaac

Same as OP.

Darksiders

Edit: Actually, it was Psychonauts. Darksiders ended first, but my first entry was Psychonauts.

HL2: Episode One

Bioshock

Torchlight

Metro 2033.

Metro 2033

I really don't remember...
I arrived on the site during the Metro 2033 big giveaway, so the points were always stuck at 300, I entered everything I saw and then when Metro 2033 was removed from the list I understood that I should keep my points for game that really interest me.

hib3

Bioshock!

Frozen Synapse.

Orcs Must Die! 2 (2 Copies)
Yeah, good times 7 months ago...

Flatout, Flatout 2

Both games I eventually bought for myself, and even gave away, I think.

Max Payne Bundle

The Ship - Complete Pack eventually it became my first win too.

Portal.

Might & Magic: Clash of Heroes.

Sequence, Terraria, and Killing Floor were the first three giveaways that I entered. And the games that I spent the most points trying to get during my first few hundred entries were Lucid and The Binding of Isaac. Lucid has about half of my first hundred entries, it seems. lol

Wizorb

From Dust.

Mine was trine too! :)

Company of Heroes lawl

Hmm...it was The Cave, according to Crazee's link.