Pep Guardiola sought a challenge at every stop of his managerial career. Whether it was swapping Barcelona B for Barcelona after just one season, moving to Bayern Munich or taking on the Premier League with Manchester City, he has usually come out on top.

On his first day at the Etihad Stadium in 2016, he admitted that, despite trophies in Spain and Germany, the question on everyone’s lips ahead of his arrival in England was: “How good is Pep?” He has already answered it once with 18 trophies in nine years in Manchester.

But amid a swirl of change at City and at the center of English soccer, he’s facing the prospect of having to answer it all over again. In a career full of challenges, this is perhaps one of the biggest yet.

Had things played out differently, Guardiola might already be enjoying his retirement on a beach in the Maldives or a golf course in Portugal. He chose to stay at City, in part, because the beginning of this past season — only the second to end without a trophy during his spell at the Etihad — was so difficult and he didn’t want to leave the club in a mess. It appears he also realized the club would find it far easier to hand over to a new manager in a summer that didn’t include the added complication of a Club World Cup.

Having decided to stay and sign a contract extension until 2027, he has taken on the task of trying to build another title-winning team. It’s just that the landscape now is very different.

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Of the squad he picked for the Champions League final against Inter Milan in Istanbul just two years ago, 15 players — including Kevin De Bruyne, Ederson, Kyle Walker and Ilkay Gündogan — have either left or been moved out to the fringes.

It’s not just the personnel who have changed. At the same time as dealing with huge squad turnover, Guardiola is also trying to adapt to what he views as a shift in the balance of the Premier League.

At one point this past season when discussing the success of teams like Newcastle, Bournemouth and Brighton, he said that “modern football is not positional, you have to ride the rhythm.” It was quite the admission from a coach who has built an empire on a strict framework of positions and movements.

After City’s Champions League defeat to Real Madrid in February, he said his “tactics don’t work like they used to.” Earlier this season he insisted he would “never ever change his beliefs” and still likes his team to make “a thousand, million passes.”

It seems, though, he has reached an acceptance that he has to change with the times.

This season, he’s trying to marry his own desire for control with more high pressing and quicker, more direct attacks to mirror what’s happening elsewhere in the league. It’s one of the reasons he picked Pep Lijnders as his assistant after the Dutchman played such a key role in developing Jürgen Klopp’s “heavy metal” style at Liverpool.

It’s a nice idea, trying to merge elements of two of the most successful teams in the modern Premier League era, but it has come with some teething problems.

After starting with an eye-catching 4-0 win at Wolves to open the 2025-26 season, City lost their next two games. In defeats to Tottenham and Brighton, they conceded almost identical goals when fast breaks exploited gaping holes at the back — gaps made more pronounced by the high defensive line favored by Lijnders.

It’s something Manchester United manager Ruben Amorim will have no doubt noticed ahead of the Manchester derby at the Etihad on Sunday. City will kick off against United one point and four places below their neighbors in the table. They’re already six points behind champions Liverpool, who can now call on new £125 million striker Alexander Isak after the international break.

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Onuoha: Man City can’t afford to lose the Manchester derby

Nedum Onuoha emphasizes the importance of winning the Manchester derby following a disappointing start to the season for Manchester City.

No team since Manchester United in 1992-93 has lost two of their first three games and still gone on to win the league. Even at this early stage, there’s a lot of ground to make up if Guardiola wants to regain the trophy he lifted six times in seven years between 2017 and 2024.

But if it’s not going to be this season for City and Guardiola, then when? Guardiola has a contract for the next two years, but staff have given up trying to predict when he might call it quits.

There’s a feeling in some corners of the City Football Academy that this could yet be his last season. There are others who feel that, even though he has admitted he’s approaching the end, the 54-year-old could still be convinced to sign another new contract. That would depend very much on his own energy levels and whether the working relationship with director of football Hugo Viana — who has taken over from Guardiola’s great friend Txiki Begiristain — is running smoothly.

Either way, City bosses decided a long time ago that Guardiola has earned the right to decide how and when he goes. He has accepted that this past season was so bad in terms of City’s specific goals that he might have been axed by any other top club.

At the end of his 26 years at United, Sir Alex Ferguson bowed out as a champion after winning the title in 2013. Guardiola’s achievements deserve the same finale.

To give himself the perfect send-off he’ll need to piece together another great team capable of thriving in a different age of the Premier League. It’s another big challenge to tick off the list.