50. Keith Gillespie

Signed from: Youth team

Debut: 2-0 win vs Bury (FA Cup tie), January 5th 1993. Scored once
League Record: Three games (+6 as sub), one goal
Sold to: Newcastle United (valued at £1,000,000 in an exchange deal), January 1995

Direct winger in the old fashioned tradition (i.e. he kept running at the full back, putting a cross in on the occasions he beat his man), Keith Gillespie scored on his debut and two years later got his only Premiership goal with a fine effort against Newcastle. They were obviously impressed as not long later he was playing for them.

I personally had high hopes for Gillespie and was disappointed to see him leave, more so when we sold Andrei Kanchelskis a few months later, as I'd not seen enough of David Beckham at that point to know he was more than capable of holding the right wing. What is interesting to wonder is that if Keith hadn't left United, whether he’d have got the chance on the right wing that was given to Beckham and making the late 90s a very different tale. Certainly his valuation of a million pounds was very high for a (relative) novice in 1995, and shows how much faith Keegan had in him.

He went on to have a fairly successful career in Geordieland and then Blackburn, where he teamed up with Mark Hughes, as well as being a regular for Northern Ireland. His last significant role was at Sheffield United, where he helped them gain promotion to the Premiership in 2006. While up there, he managed to get sent off within seconds of coming on as a sub, for elbowing an opposition player in the face while he ran into position. Bizarre.

Still playing in the League of Ireland as of 2012.