Now aged 26, he made his debut for hometown club Coventry City in 1999 aged just 16.
Always popular with the Sky Blues fans, the striker failed to get a look in under a number of managers and was close to leaving the club on more than one occasion.
First Eric Black and the Micky Adams showed more faith in him however and it was playing as a left-winger under Adams that McSheffrey enjoyed a superb season in 2005/06, scoring 17 goals and creating countless more.
That earned a move to Birmingham but injury problems have not helped the player nail down a regular first-team place.