Coventry City McSheffrey was born in
Coventry, and began his football career at home town club
Coventry City. When he made his first-team debut against local rivals
Aston Villa at the age of 16 years and 198 days on 27 February 1999, a game that Coventry won 4–1, he became the youngest player ever to play in the
Premier League. He held the record for over four years until
Aaron Lennon made his
Leeds United debut at a younger age in August 2003. During his time at Coventry he spent loan spells at
Stockport County,
Luton Town earlier in the
2004–05 season helping them achieve promotion to the
Championship, and Swedish side
IK Brage. Playing primarily on the left wing in the
2005–06 season, McSheffrey ended up among the top scorers in the
Football League Championship with 15 league goals. It was form like this that brought him to the attention of local rivals
Birmingham City during the summer of 2006. After weeks of bidding, Coventry accepted an offer valued at £4 million. This has since been estimated at £2.3m cash with a further £1.3m depending on promotion and appearances. The deal was completed on 16 August 2006, and McSheffrey became a Birmingham City player three days after his 24th birthday.
Birmingham City McSheffrey scored his first
hat-trick for his new club in a league match against
Preston North End on 9 December 2006. He was part of the
2006–07 promotion-winning side, returning to the Premier League after just one season in the Championship. McSheffrey was also their top scorer with 16 goals, of which 13 were scored in the league. His
penalty in Birmingham's 3–2 win against
Tottenham Hotspur at
White Hart Lane on 2 December 2007 was his first goal in the Premier League. McSheffrey found his time limited during the
2008–09 season; he helped the side clinch promotion back to the Premier League by winning four out of six league appearances he made. and then to have returned to Birmingham because he needed surgery on a persistent knee problem, but manager
Alex McLeish confirmed that the loan was in fact for two months. Told in August 2009 that he was free to find another club, and frustrated by lack of opportunity, McSheffrey made just one start and four substitute appearances in the
2009–10 Premier League. He made his debut the following day, producing a
man-of-the-match performance on the left wing in Leeds' 2–0 League home win against
Colchester United. In an interview after the game McSheffrey said "there'd be no better club to be with at Championship level" should Leeds succeed in gaining promotion. Ineligible for an FA Cup replay against
Tottenham Hotspur, McSheffrey returned to the starting line-up for the 2–2 draw with
Hartlepool United. He scored his first and only goal for Leeds against
Walsall after his mis-hit cross eluded goalkeeper
Clayton Ince, but Walsall won 2–1 to inflict Leeds' first home defeat in more than a year. McSheffrey was dropped to the bench against
Oldham Athletic and replaced in the starting line-up by
Aidan White, but after White suffered an injury McSheffrey returned to Leeds' starting line-up against
Huddersfield Town. McSheffrey earned promotion with Leeds to the Championship, after finishing as runners up in League One.
Return to Coventry City In May 2010, Birmingham City announced that McSheffrey was one of five players to be released when their contracts expired at the end of June. He agreed to return to Championship club Coventry City, where he agreed a one-year deal, with the option of a further year, to begin on 1 July 2010. His return to Coventry was a largely disappointing spell in his career, despite being a regular starter, fans felt that his best years were past him. McSheffrey was one of eight players told in June 2013 that they did not feature in manager
Steven Pressley's future plans, and one of five who had to train on their own during pre-season. On 3 September, his contract was cancelled.
Chesterfield Ten days later, he signed a four-month contract with
League Two club
Chesterfield.
Scunthorpe United On 14 January 2014, McSheffrey signed for
Scunthorpe United until the end of the
2013–14 season. McSheffrey made his United debut on 25 January in a 3–3 draw away to
Dagenham & Redbridge, and his home debut two days later in a goalless draw with
Fleetwood. He played 37 times for United in the league that season, scoring four goals,
Eastleigh McSheffrey joined
National League club
Eastleigh on 7 September 2017 on a deal until January 2018. He scored twice from 11 league appearances before his contract was cancelled by mutual consent for family reasons in late November.
Grimsby Town McSheffrey joined League Two club
Grimsby Town as a
free agent on 15 March 2018 until the end of the season. He was released at the end of the season. ==Coaching career==