Medal title: Think fast
To qualify: Play a map for the first time and win your first 5 games on that map.
As a lot of people have said, if you play a lot of games you will win most of the medals out there. This one is different - every time you fail to win on a new map you could never qualify for this medal on it. It would take real skill to achieve with no practice first !!!
I would suggest 1,3 & 5 for Bronze/Silver/Gold - i have a couple of maps i have played once or twice and have 100% record on, but 5 would be tough !