Awarded to him by Gordon Strachan at Villa Park at the age of 16 on February 27, 1999, he became the youngest player to play for the club as well as the youngest to play in the Premier League in the 4-1 beating arc rivals Aston Villa.
McSheffrey then spent 14 seasons in the top two divisions of English football in a professional career that spanned almost two decades.
Born and raised in Coventry, he had a few stays with the Sky Blues. Reached the top with Birmingham City and also had loan moves with Leeds United and Nottingham Forest.
In an exclusive interview with our sister title BirminghamLive, the 37-year-old gave an honest look at his time in professional gaming and the stories behind his moves, including those that didn’t happen.
Moving from Sky Blues to Blues (2006)
“I remember being in America with Coventry for pre-season training, Micky Adams called me and said he had an offer,” Steve Bruce offered you a million pounds, I told him where to go. What do you think, you don’t want to leave here, do you? ”
“I said” no, not really. ” Maybe at the time I was a bit naive about football movements, I had never done anything.
“I was 23 before I was 24 and I have been in Coventry since I was about nine. There was never any question of wanting to leave, we were always in the Field hoping to enter the play-offs and all that was always never to chase after anything.
“The summer before Reading was really exciting and I went to meet Brian McDermott and Nick Hammond and they were in the same league as Coventry and I saw it as a side move at the time.
“Especially since Coventry was moving to Ricoh and as a local boy, I thought I should play in the new stadium, so I turned it down.
“This is the season where they got 106 points!
“I didn’t think about it, I had another good season and the following summer, Birmingham showed interest. Even then, I just continued my training.
“A few offers were received over the course of a few weeks and when the pressure came it was like” I don’t really want to leave Coventry “but I watched the Birmingham team and it was better than the team of the summer before that wanted me.
“Each child’s ambition is to play Premier League football and I thought” this is not a side move, they just fell, Bruce had recruited very well “and I thought it was a good shot.
“It was difficult to leave Coventry, but in the end I was in a Birmingham team that was the best draw for that level and it turned out to be the case.
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“I scored the winner on the first day of the season with Coventry, and then I didn’t score for the Blues in seven or eight games.
“I remember bringing in a few assists and once I scored it was like the chains were not in place, I got something like eight of eight and I had 15 for the Blues just before the start of the year. I was probably the most confident I have ever been.
“The goals were fluid, the assists and I was playing with freedom and I was happy with my level of performance. “
Back in the Premier League (2007/08)
“We went up, started the season, then Bruce went to Wigan and Alex McLeish arrived around November.
“We went up there and there was a lot of hype about it, that summer I had the most interviews I have ever had in my life.
“I remember doing most of the interviews and it was all about Premiership football, I tasted it with Coventry when I was a kid and it took me up to 24 years to get back. “
He made 30 against 38 starts in his first elite season before lowering McLeish’s plans and plans and being sent on short loan periods to Nottingham Forest and Leeds United for his return to the House.
Return to Coventry (June 2010)
“There were about three interested solid clubs, I met [Phil] Parkinson and Charlton and had a good chat with him and Aidy Boothroyd who had just entered Cov.
“It was just a breath of fresh air for me at a time when I needed someone to put my arm around and fill me with confidence.
“He was almost like a sports psychologist who made you feel good about yourself. It gave me the boost I needed.
“I felt like I had done the first season or two well.
“I knew I turned into a better versatile and educated player, I had this broad role as a midfielder at a tee. I knew everything about it in and out of possession.
“But I left after scoring 17 goals per season for three seasons on the spin, I went back and scored nine points and I remember people saying” This is not the same player “.
“In the end, I thought I was fine, but I probably lost my lead, that meter of pace and excitement – but I felt like I was becoming a real team player. “