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Sounds like your Xbox is doing you a favour, to be honest! Free roles should be reserved solely for those special midfielders and forwards who are graced with silky technical ability, and can float around the pitch causing havok whenever they receive the ball. If five of your players have free roles and are all playing at the same time your team would crumble into absolute disarray. Perhaps if you limit the number of players who have free roles to just one, you might see a difference.
If you have an issue such as this with the match engine then would you mind reporting it in the FM2008 Bugs Forum as the 360 uses the same code as the 8.0.2 PC Patch, thanks.
just because most managers dont have the balls to do so doesnt mean that more than one player on free roles is a mistake.
if you can keep the ball then what is the point of having players stuck in the same position? more movement, the better. its my phillosophy, so the game isnt doing me a favour by not listening to my instructions ill have you know!
if you keep the ball well enough you could have your whole team on free roles...
so much for free roles? 
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