Manchester City have been close to perfect in the transfer market over the last eight years but, as Kalvin Phillips proves, they have had some major misses as well.
Pep Guardiola, in conjunction with the club’s board, has assembled one of the best football squads of all time and have enjoyed unprecedented success in the Premier League as a result.
Manchester City became the first team in English top-flight history to win the league four years in a row last season and became the second English team to win the treble the year prior.
That sort of dominance doesn’t happen without excellent recruitment and City have been second to none in scouting and signing world-class talent.
However, while the vast majority of signings have gone on to achieve greatness, Guardiola has recruited a few players that just haven’t worked out.
Kalvin Phillips, who looks set to leave the club on loan to Ipswich Town, is just one of them. Here are the rest of Guardiola’s biggest City transfer flops.
- Who is Kalvin Phillips? Get to know the midfielder who could leave Man City in the transfer window
Kalvin Phillips

Kalvin Phillips was signed for the steep price of £45m from Leeds United in 2022 to replace departed captain Fernandinho and provide much-needed backup for Rodri.
However, things did not go to plan. Phillips’ first months at the club were injury-ridden and then a comment on his weight from Guardiola shattered any remaining confidence.
Even when Rodri was unavailable, Phillips was not trusted to start and he spent the last half of 2023/24 on loan at West Ham United. Things did not get any better for him in London.
Now Phillips is set to join newly promoted Ipswich for the season but, with a contract until 2028, it’s hard to see him leaving City permanently any time soon.
Claudio Bravo

Guardiola immediately ruffled feathers upon taking over at City by making it clear Joe Hart was not in his plans as the goalkeeper was not good enough in possession.
The City hero was immediately ousted but, while it’s clear Guardiola made the right decision, his first pick to replace Hart had many doubting the new City boss.
Claudio Bravo was signed from Barcelona and after making a calamitous mistake on his debut in the Manchester derby, the Chilean never got better and struggled to adapt to the vigours of the Premier League.
Bravo served as a decent backup until 2020 but was replaced as No.1 by Ederson the following season.
Angelino

It’s not often City actually utilise the buy-back clause they insert in most of their sales but in the case of Angelino in 2019, that’s exactly what they did.
The Spaniard was brought back from PSV Eindhoven in a £12m deal to provide left-back cover but his limited performances were costly to the team.
A surprising start against title rivals Liverpool was the nadir when he was beaten time and again on his flank in the 3-1 defeat.
Angelino lasted until January until being loaned out to RB Leipzig and joined them permanently the following summer. He signed for Roma this year after a spell in Turkey.
- Man City summer transfer window 2024: Confirmed signings, departures, loan exits and releases
Matheus Nunes

The jury is still out on Matheus Nunes but things do not look promising after his debut season at the club.
City splashed out £54m to bring the all-action midfielder in from Wolves in 2023 but he struggled to establish himself in the side, registering just 1,540 minutes.
There is still time for Nunes to turn things around but he will have to start the next season strongly or he could be following Phillips out of the door.
Nolito

It’s easy to forget that Nolito was actually a Guardiola signing and one of his first at the club, with the forward arriving from Celta Vigo in 2016.
Nolito would last just one season in Manchester and largely played a periphery role. However, despite seeing just 1,351 minutes of action, he still managed to score six goals and provide five assists.
Now retired, the Spaniard made just nine Premier League starts, though, and decided to leave after struggling to settle in the North West.
