Rank/Rate players over time?

One thing that you've got to take into account when doing this is, losing players generally do not enjoy being reminded that they really suck. Most likely, you've got a player in your crew that NEVER wins. Most home games between friends do. A word of advice, if you want him to continue playing with you guys, consider scrapping this whole "Player of the Year" Idea and just double the buy in for more interesting poker.