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In FM14 I took over Aston Villa just after it had relegated. My top wingback wanted to transfer and was upset that I hadn't let him go. By November-ish, I had a 10 point lead on the rest of the league and he withdrew his request.
Not an identical situation, as I don't believe that his contract was coming up at the end of the season and I was not the manager that drove the bus through the losing battle with relegation. But, for whatever it is worth, he retired a Villan after several more years at left back.
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