The belief that he could have been a Champions League winner had Rafa Benitez put him in the Kop team still gnaws away.
Crouch told The Sun: "Looking back, it was an achievement to get to the final and I'm very proud we did that - but I was very angry and disappointed not to start.
"I'd scored seven in the Champions League that year, was our top scorer in all competitions and I felt good. I was expecting to play and was really disappointed when I found I was on the bench.
"I genuinely believe that, although Milan were a fantastic team, we could have beaten them so it was frustrating that I didn't get more of a chance. It was still a great achievement to get to the final with the players and the teams that are in the Champions League.
"But the loser's medal isn't quite what you are looking for. I have the medal on display but it's tucked in behind the FA Cup winner's medal I got when we beat West Ham the year before.
"It's true I look back on it with regrets.
"I think we could have won it and it still hurts that I didn't get enough chance on the pitch. There's some unfinished business for me against them, without a doubt."