Either way, I don't think we have any way to say that it should be a Fly-Eagles-Fly - Waredude game. When the game between tomato - tugwash is finished, the ratings will look different.
True. I was just using as an example, since we are currently the two highest rated except for you, Junebug (who just lost a challenge game, I think), and CaptainTugWash.
I think rating is a lot better than winrate. Winrate ignores the strength of your opponents and your old losses will always follow you. Rating will depend on the strength of your opponents and the most recent results matters more than old results.