Just a while ago, I fired up my long-neglected PS2, loaded the Winning Eleven 7 after these years and just randomly played a match.
I haven't had this satisfied feeling after a match from a football game for a long time. This is the reason why PES/Winning Eleven is the best football game, not the crap they produce in recent years. In the past, I could play this game with friends for hours and hours and not get bored. Sadly, gameplay seemed to take the backseat against graphics in recent times.
Best game would probably be Winning Eleven 7 or ISS Pro Evolution 2 on the PS. Those were the game I had the most fun with.