I don't think that comparing Winning Eleven to Madden in terms of money plays is really fair. Soccer is pretty different from football, it's a more free flowing game.
There are two distinct types of money in my opinion :
1. Plays that can't be stopped regardless of what defense is used. This is the real money play and you can take it to the bank all day.
2. Plays that can be stopped by a defensive play, but the CPU never calls that play - therefore making it money against the CPU.
#2 Could be squashed by better defensive playcalling by the CPU. And, this is what I believe the original poster is referring to. "Why doesn't the CPU adjust to what I am doing and calling a defense that will stop this play ?"