#3 Kieran Richardson
It's always going to be hard when you are trying to force your way into the United first team at the same time as Cristiano Ronaldo, but Richardson had plenty of talent, equally capable of playing in midfield and defence.
However, despite this versatility, things never really worked out for him at United, although he was still a valuable squad member for a few years without ever getting a sustained run in the first team.
Richardson also developed something of a reputation for being more focused on his possessions than his actual football, and after a number of loan spells, he moved to Sunderland in 2007.
In his 5 years there, he drifted in and out of the first team whilst Sunderland battled relegation. A similar trend followed following moves to Fulham and Aston Villa.