Yeah i could easily see it going awry with regards to postion. How did you go about your random generation? Did you use a random number generator and have id's assigned to each player.
Also im not sure on the math so i thought i would ask. If you took the top 300 applied a true random order wouldnt you technically come closest to the mean of all the players? I would think that a team close to the mean would have to beat at least a few owners?