I'm not sure I understand this. 2Dcube has a gold medal on EVERY ONE of his games yet there have only been 2 competitions held. How do you enter you game for a chance to get a medal?

They're just staff picks, and not won in a competition. (I believe)

Oh, man I want wanna my games to get staff picked. I don't know what's wrong with them cause people never leave in depth comments. =/

Don't give up, maybe you'll make an outstanding game that will survive the test of time and the staff will have to pick it.

That would be nice and having one of my games staff picked would lift my spirit and probably make me better =]

Lol, just don't think about making a game for staff pick, if you do, you'll go overboard and make a potentally good game into a not so good game, kind of like me with rushing things, I rushed my 2nd demo for Ultimate Ping Pong and it isn't as good as it could've been.

I think actually the medal refers to the member, NOT the game.

Yes, that's correct.
2dcube won the first competition, so he has a gold medal near his name.
The author whose game made the 2nd place has a silver medal and the third has a bronze medal.