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John Fleck, once famously dubbed the 'Scottish Wayne Rooney' during his days at Rangers, went on to become one of Chris Wilder’s most astute signings at Sheffield United.

When Wilder took charge at Bramall Lane ahead of the 2016/17 season, he brought in Fleck on a free transfer — a move that would turn out to be a masterstroke.

The Scottish midfielder had previously spent four seasons at Coventry City in League One, joining them in 2012 after leaving Rangers. During his time with the Sky Blues, he made 182 league appearances and netted eight goals. Although Coventry suffered relegation that season, Fleck’s journey in South Yorkshire would bring far greater success.

Fleck’s story began at Rangers, where he made his debut for the Glasgow giants at just 16 years old. His early promise led many to compare him to Manchester United legend Wayne Rooney. Speaking to Sky Sports in 2010, Fleck said, “I’m still a young boy and I think people expected me just to come out and be like Wayne Rooney every week but that’s not going to happen.” He added, “He’s a world-class player and it takes time for a young boy to come through. I’m willing to be patient but hopefully I’ll get my chance.”

Following Rangers’ liquidation in 2012, Fleck joined Coventry City amid high expectations. His potential initially went unfulfilled until Steven Pressley shifted him into a deeper central midfield role, where he began to dictate games and showcase his technical ability.

By the time Sheffield United came knocking, Fleck had established himself as one of the best midfielders in the division. At the end of the 2015/16 campaign, he swept Coventry’s end-of-season awards, picking up both the Players’ Player and Supporters’ Player of the Year honours.

Fleck’s first season at Sheffield United was nothing short of spectacular. He contributed 20 assists across all competitions as the Blades clinched the League One title. His seamless transition into Championship football followed, with 41 league appearances in 2017/18 and 45 in 2018/19, helping Wilder’s side secure promotion to the Premier League for the first time in 12 years.

In 2019, Fleck’s performances earned him a call-up to the Scotland national team. Wilder said at the time, “He thoroughly deserves it as he’s been incredible. We brought him in on a free transfer from Coventry when we were in League One and he’s embraced every level since and moved forward.”

By early 2020, Fleck’s growing reputation had drawn interest from West Ham United, who reportedly submitted a £4 million offer according to The Athletic, but Sheffield United swiftly rejected the bid.

Under Wilder, Fleck’s value extended beyond his passing and composure. The manager managed to rediscover the attacking qualities Fleck had shown in his youth. Speaking to The Star in January 2020, Wilder explained, “He started out as a centre-forward. Technically he’s really good. That was John’s position to begin with, I believe. That’s why he knows what he’s doing and has got the ability.”

Instead of restricting him to a defensive midfield role, Wilder encouraged Fleck to make forward runs and arrive late into attacking positions — a tactical freedom that revitalised his game.

When Fleck quietly left for Blackburn Rovers in February 2024 at the age of 34, he had made 278 appearances for Sheffield United in all competitions, scoring 16 goals and providing 48 assists.

For a player signed on a free transfer to deliver three promotions and countless key performances, it’s no exaggeration to say that Sheffield United truly struck gold with John Fleck.

After narrowly missing out on promotion to League One with Chesterfield — losing to Notts County in the play-off final — Fleck now finds himself a free agent, looking for the next chapter in his career.