I just went through the topics from the last 5 years and my head's still quite empty. Aslo, I suck at naming awards, perhaps someone could 'translate' them from Mikachuese to English XD and that's also why I think they need some clarification.

Quickest Strategist (comes up fast with killer strategies and posts them at once)
Most Patient Trainer (like doesn't care if the battle lasts for a long time, or takes evolving Pokemon as projects or something)
A Match You'd Like To See
Greatest Comeback
Someone Who You'd Like To Make A Comeback (somehow, I don't really know if this one's right, just a quick idea)
Most Elegant Team (not necessarily the strongest or the most versatile one, but someone who's been faithful to his or her style could have this)
Most Surprising Trainer
Most Originally-Colored Pokemon (as in a sprite)
MOTY

More to come ooooor not!