MANCHESTER, ENGLAND – JANUARY 28: Leroy Sane of Galatasaray during the UEFA Champions League 2025/26 League Phase MD8 match between Manchester City and Galatasaray A.S. at City of Manchester Stadium on January 28, 2026 in Manchester, United Kingdom. (Photo by Robbie Jay Barratt – AMA/Getty Images)
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It was Pep Guardiola’s second season that Manchester City developed into the all-conquering machine that would dominate English soccer for the best part of a decade.
Re-tooled with new signings, the defensive inadequacies and erratic finishing that had held the club back during his first campaign were eradicated.
Leroy Sane, a young German winger, joined City as a teenager and soon turned his raw talent into consistent elite performances.
Blessed with pace, trickery and devastating left foot, he was often the one to pick a way through the massed rows of opposition defenders Guardiola’s teams frequently faced.
By his third season, rumors of Sane’s departure and injuries surfaced, clouding his trajectory.
City won back-to-back league titles as Sane’s key goal against Liverpool secured their Premier League crown.
By 2019, Sane’s contract was winding down, and City doubted his willingness to renew.
A transfer to Bayern Munich was reportedly agreed only for the move to be abandoned when Sane injured his anterior cruciate ligament in the pre-season opener against Liverpool.
The setback only delayed the inevitable; Sane exited for Bayern Munich the following year, in 2020.
MUNICH, GERMANY – APRIL 30: Leroy Sane of Bayern Munich celebrates scoring his team’s first goal during the UEFA Champions League semi-final first leg match between FC Bayern München and Real Madrid at Allianz Arena on April 30, 2024 in Munich, Germany. (Photo by Alexander Hassenstein/Getty Images)
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At the time, Sane joined the reigning Champions League winners, seemingly moving to a club promising European success—something City had not yet achieved, fuelling the sense of missed opportunity.
The hope was that the German would reach the superstar level of Robert Lewandowski or Arjen Robben in Bavaria.
At Bayern, titles came but managerial turnover and inconsistency prevented European dominance.
Sane often hinted at greatness but, while his time in Munich was far from poor, he never quite reached the peak many believed possible—leaving the sense that his career might have soared higher down another path.
His move to Galatasaray brought resignation and a sense of regret, echoing his earlier transfers.
His return to North West England in the red and yellow jersey of Galatasaray for a high-profile Champions League clash raised the question underpinning his career’s arc since leaving City: What might have happened if he had stayed?
“Leroy gave us something unique,” Pep Guardiola reflected ahead of the reunion.
“He was a special player and had an unbelievable connection with the midfield, especially Kevin [De Bruyne].”
Sane, who also spoke to the media ahead of the game said he’d never lost contact with either the coach or his former teammates
“I’ve never truly lost touch with some friends at the club. I’m looking forward to seeing some old friends again on Wednesday,” he said.
Sane went on to describe Guardiola as “the definitive architect of modern football” adding that the Catalan coach had “completely reprogrammed my footballing brain”.
He added: “Pep shows you a different sport entirely. His tactical demands are relentless, but he didn’t just coach me — he evolved me. I left his guidance as a far more complete player than I ever thought possible.”
After Sane left, City’s level was further raised; the team ended its elusive wait for a Champions League title in Istanbul in the summer of 2023.
It is hard not to wonder if consistent coaching under Guardiola, rather than several managerial changes at Bayern, would have fostered Sane’s full potential, further deepening the sense of what City lost and what Sane himself may have missed.
Guardiola was always a stern taskmaster with Sane, never overly praising him and often reeling back giddy reporters keen to hype the German star.
But there are no givens. It’s not as if his coaches in Munich were slackers. Quite to the contrary, they were some of the best managers in world soccer.
There’s no guarentee he would have flourished by staying put either.
In the years since Sane left Manchester in 2020, the City squad has changed considerably.
It is only the quartet of Rodri, Phil Foden, Bernardo Silva and John Stones who remain from his last last season with City.
When asked by the media to reflect on that change, Sane was complimentary: “It shows that at a club like City, evolution never stops. Legends like Kevin [De Bruyne] or Ilkay [Gundogan] moved on because sometimes you need a new horizon after winning it all. But make no mistake: at City, the pressure is constant. If you don’t perform at the highest level every single week, the club is built to move forward — with or without you.”
Ultimately when Sane took to the field in Manchester he did not deliver a display that rolled back the years and reminded the fans what they’d missed.
Galatasaray lost 2-0 in what was a relatively comfortable win for City.
It seems fitting that a relationship characterized by lingering regret concluded with another small disappointment, as regret remains the defining note of Sane’s connection with Manchester City.