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Heskey struck 60 goals in 223 games for Liverpool after becoming the club's record signing when he joined for £11m from Derby County in 2000.
However, following manager Gerard Houllier's departure in 2004, Heskey was sold to Birmingham City for £6.25m.
But it could have been Milan rather than the Midlands for the now 47-year-old, who admits he didn't even know who managed the Serie A giants at the time.
It was Carlo Ancelotti leading the Rossoneri, and his Milan side would meet Liverpool in the final of the Champions League the following May, losing on penalties after surrending a 3-0 lead to draw 3-3 with Rafael Benitez's Reds.
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Asked which was the most interesting side he almost joined, Heskey pointed to the Italian giants.
Speaking to Prime Casino, Heskey said: "AC MIlan.
I was leaving Liverpool and I was talking to AC Milan about the possibility of going there, but I ended up in Birmingham.
"I’m not too sure who the manager was to be honest.
a UEFA Super Cup followed before another League Cup was won in 2003.
And Heskey admits that Liverpool's achievements in that era have often been overlooked.
He said: "I mean, we definitely get credit from Liverpool fans for what we did.
You go to three cup finals, win them all - amazing.
"The reason we don’t get the credit from neutrals is because we didn’t win the league, and because the UEFA Cup isn’t as prestigious as the Champions League.
We used to watch the FA Cup on television, everyone would be interested.
"Then the UEFA Cup, yes, it's the one below the Champions League, but it's still huge.