Eight years later, the Midlands club may regret not offering a better deal, as John Fleck went on to prove himself as one of the Championship’s standout midfielders during his time with Sheffield United.
The former Rangers player became a key figure in the Blades squad that surprised many in the 2019–20 Premier League season by finishing ninth. That success, however, might never have happened if he hadn’t chosen to leave Coventry in 2016—a decision Sheffield United supporters remain thankful for.
After making 57 appearances for his boyhood club Rangers, Fleck left Ibrox in 2012 at the age of 20 in search of regular first-team football. He joined Coventry City in League One, where he gradually established himself as an important player.
Although his start at Coventry was slow, he became a regular during the 2013–14 season and continued to improve in the years that followed. His breakthrough came in the 2015–16 campaign, when he made over 40 league appearances and formed a strong midfield partnership with Romain Vincelot.
Manager Tony Mowbray famously described him as the “oil in our machine,” highlighting his importance to the team. His performances that season earned him both the supporters’ and players’ Player of the Year awards.
Fleck’s form attracted interest from several clubs, and despite Coventry offering him a new contract, he chose to move to Sheffield United, signing a three-year deal.
He made an immediate impact at Bramall Lane, playing a vital role in helping the Blades secure promotion to the Championship. Operating from deep in midfield, he recorded an impressive 17 assists and four goals.
While his numbers dipped slightly in the higher division, his strong understanding with manager Chris Wilder ensured he remained influential. In his first Championship season with Sheffield United, he contributed eight assists as the team finished 10th.
Building on that progress, Fleck—alongside Mark Duffy and Oliver Norwood—helped push the team into promotion contention the following season. They exceeded expectations by securing automatic promotion to the Premier League, finishing ahead of Leeds United.
During that campaign, Fleck remained a key creative force, producing 71 chances and registering 10 assists. His performances earned him the opportunity to play in the top flight, capping off an outstanding three-year spell in the EFL under Wilder.
