9. Matthew Kilgallon
Matthew Kilgallon was rarely considered a first-choice defender during his time at Leeds United but he was getting game time in the Championship so it was somewhat of a surprise when he took the risk to join Premier League Sheffield United.
The fact that Leeds required funds and Kilgallon wanted to try to make it in the top flight probably played a large part in his decision but it was an unnecessary risk at that stage of his career and he made just six appearances as the Blades were relegated to the second tier.
Kilgallon would establish himself in the centre of defence at Bramall Lane but he could not help them to a return to the top flight. Sunderland came calling but over the course of a three-and-a-half year contract, he made just 23 top-flight appearances for the Black Cats.
Would the defender had benefited from remaining at Leeds longer than he did? It's debatable but in all of his years as a professional footballer, he has only made more than 30 league appearances in a league season on two occasions, perhaps a sign he left Leeds too early.