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McSheffrey joined EFL League Two side Grimsby Town as a free agent on 15 March 2018 until the end of the season. He was released by Grimsby at the end of the 2017–18 season.

On 18 July 2018 McSheffrey played on trial for Boston United in their Lincolnshire Senior Cup defeat against Lincoln United.

In 2018, McSheffrey joined the coaching staff at Doncaster Rovers' Academy as professional development phase coach working with the under-18 team. Alongside his coaching role, he played a few matches for Northern Premier League East side Frickley Athletic early in the 2018–19 season.

On 7 September 2017, McSheffrey joined National League side Eastleigh 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.

On 23 March 2016, McSheffrey signed for fellow League One club Doncaster Rovers on loan until the end of the season.

On 14 January 2014, McSheffrey signed for Scunthorpe United until the end of the 2013–14 season. McSheffrey made his United debut on 9 August 2014, in a 3–1 defeat against Swindon Town. He made his home debut the following week, in a 4–0 defeat to Preston North End, and scored his first goal for the club on 30 August 2015 in a 2–1 win against Walsall. He played 37 times for United in the league that season, scoring four goals, as they finished 16th behind Oldham Athletic by one point.

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 started on the left wing for Leeds against Carlisle United in the Football League Trophy Northern Final second leg. Leeds won the game 3–2, but ended up losing the tie after losing the penalty shootout 6–5, with McSheffrey converting one of the penalties for Leeds.

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.

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.

He made more than 450 appearances in the Football League and Premier League, including 247 for Coventry City, where he became the youngest player ever to play in the Premier League. He went on to play for Stockport County, Luton Town, Birmingham City, Nottingham Forest and Leeds United before returning to Coventry in 2010. Released in September 2013, he signed for Chesterfield later that month. In January 2014 he signed for Scunthorpe United on a free transfer until the end of the 2013–14 season before moving on to Doncaster Rovers, Eastleigh, Grimsby Town and Frickley Athletic. He scored more than 100 league goals during his career.

On 29 January 2010, McSheffrey joined Leeds United of Football League One on loan for the remainder of the season. 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.

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.

Due to his need for surgery on a persistent knee injury, he was reported to have returned to Birmingham, but manager Alex McLeish confirmed he was still on loan at Forest. 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.

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.

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, seeing Birmingham promoted into 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. On 2 December 2007 he converted a penalty in Birmingham's 3–2 win against Tottenham Hotspur at White Hart Lane to score 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. In March 2009, he joined Nottingham Forest on loan for an initial period of 29 days.

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. He represented England at under-18 and under-20 levels.

Gary McSheffrey (born 13 August 1982) is an English former professional footballer who played as a striker or left winger. Since 2018, he has been part of the under-18s coaching team at Doncaster Rovers, one of his former clubs as a player.