I used to play Konami's Winning Eleven 9 on the original xbox. Co-worker of mine, Ireland, wants to give one a shot. Never really cared for EA's FIFA series, but 2009 looks good. I may give that or Pro Evolution Soccer a chance with him.
I always get the FIFA games. I like having the real players and teams myself. The new online mode for FIFA 09 looks like it could be pretty cool where you play 10 on 10 with all real people..only the keeper is computer controlled.