Man City crisis: Nine biggest transfer mistakes that have caused Pep Guardiola downfall

Man City manager Pep Guardiola has made some mistakes in the transfer market

Manchester City manager Pep Guardiola has made some brilliant signings over the years – but he doesn’t always get it right in the transfer market.

City are enduring their worst-ever season under Guardiola, who has admitted that his side have “no chance” of winning the Premier League title in 2025.

While Rodri’s anterior cruciate ligament injury derailed their campaign, City’s recent struggles can be partly attributed to their work in the transfer market.

We’ve taken a look at 10 of the biggest mistakes Guardiola has made in the transfer market, including both signings and sales.

Jack Grealish

Manchester City signed Jack Grealish in the summer of 2021 after triggering the £100million release clause in his Aston Villa contract.

The deal made him the most expensive Premier League player of all time, although he has since been usurped by Enzo Fernandez, Moises Caicedo and Declan Rice.

He has failed to justify that price tag over the last three-and-a-half years, registering just 14 goals and 20 assists in 143 appearances in all competitions.

Admittedly, the winger played an underrated role in City’s historic treble triumph in the 2022/23 season but a £100million player should be producing more than one good season.

He played a bit-part role in the 2021/22 and 2023/24 campaigns and has started just six Premier League games this season.

According to reports, City are willing to sell the 29-year-old but they will struggle to recoup even half of what they paid for him in 2021.

Jack Grealish didn’t score a goal for Manchester City in 2024. His last goal came against Crystal Palace on December 16, 2023. pic.twitter.com/iMU6PYHdx2 — ESPN FC (@ESPNFC) December 29, 2024

Kalvin Phillips

Despite already having Rodri at the club, Guardiola decided to sign Phillips from Leeds United in a £42million deal in the summer of 2022.

He failed to dislodge the Spain international from the side and played a bit-part role, making just six starts and 25 substitute appearances in all competitions.

The England international also looked ill-suited to Guardiola’s style of football and was unable to produce his best form at the Etihad.

“Marcelo (Bielsa) gave Kalvin the best of Kalvin in his career,” Guardiola said. “I’d love to have done with Kalvin what Marcelo has done to him.

“We have our own specific way to play and (he) sometimes struggles in a few things, while the previous (Leeds playing style) was perfect (for him).”

He had a disastrous loan spell at West Ham United in the second half of the 2023/24 season and is spending the current campaign on loan at Ipswich Town.

Romeo Lavia

After signing Phillips from Leeds, City sanctioned Lavia’s departure two days later and let him join Southampton for just £10.5million.

The midfielder impressed during his solitary season with the Saints and established himself as one of the best young players in the Premier League.

Chelsea fought off competition from Liverpool to sign Lavia in a deal worth an initial £53million and another £5million in potential add-ons.

He endured an injury-plagued debut season at Stamford Bridge but has since produced some brilliant performances under Enzo Maresca.

City will now be regretting their decision to sell the Belgium international, who would’ve been able to fill to void left by Rodri’s injury.

Romeo Lavia is frustrated by his situation at Chelsea

Romeo Lavia is frustrated by his situation at Chelsea

Matheus Nunes

City initially pursued Lucas Paqueta in the summer of 2023 but abandoned plans to sign the West Ham United midfielder after he was subject to a betting investigation.

They switched their attention to Nunes and signed the Portugal international from Wolves on transfer deadline day for £53million.

He played a bit-part role in his debut season, making just seven starts and a further 10 substitute appearances for City in the Premier League.

The 26-year-old has had more opportunities in 2024/25 but has also made some costly errors, conceding penalties in their defeats against Sporting CP and Manchester United.

Jeremy Doku

After Riyad Mahrez joined Saudi Pro League side Al-Ahli in 2023, City identified Doku as the ideal replacement for the Algeria international.

They forked out a reported £55.5million to sign the winger from Rennes, making him the eight-most expensive signing in City’s history.

While he has shown glimpses of his talent at the Etihad, the 22-year-old has often been criticised for his inconsistency and lack of end product.

He has netted just five Premier League goals during his first year-and-a-half in England and four of his 13 assists came in one game against Bournemouth.

City could’ve signed Mohammed Kudus from Ajax in the same summer for an upfront fee of £35.4million or kept Cole Palmer instead.

Cole Palmer

The aforementioned Palmer came through the academy at City and made 41 first-team appearances for the club but struggled to cement a regular place in Guardiola’s side.

He has admitted that he wanted to go out on loan for the 2023/24 season but City sold him to Chelsea on transfer deadline day in a deal worth £42.5million.

The England international enjoyed a remarkable debut season at Stamford Bridge, registering 22 goals and 11 assists in 33 Premier League appearances.

“I said many times, I didn’t give him the minutes that he maybe deserved and wanted, the minutes he now has at Chelsea,” Guardiola admitted last season.

“I understand that completely. I am happy for him because he is a lovely guy. He is playing good and is an incredible threat.”

He’s maintained that brilliant form in 2024/25 and no City player has more Premier League goal contributions than the 22-year-old in the last 18 months.

Effortless elegance from Cole Palmer 🩰 pic.twitter.com/TfU7YBw3BW — Premier League (@premierleague) December 30, 2024

Liam Delap

Delap was prolific for Manchester City at youth level but only played 170 minutes for the first team, scoring one goal in a Carabao Cup win over Bournemouth.

He had loan spells at Stoke City, Preston North End and Hull City before joining Ipswich Town in the summer in a deal worth an initial £15million.

The 21-year-old has made an immediate impact at Portman Road, registering seven goals and two assists in 18 Premier League appearances this season.

He is now one of the most sought-after strikers in English football and has been linked with Chelsea, Arsenal, Tottenham and Manchester United.

City also sold Julian Alvarez to Atletico Madrid in the summer and didn’t sign a replacement, leaving Erling Haaland as the only recognised senior striker in the City squad.

Delap has shown that he can play in the Premier League and would have been a perfect player to operate as the understudy to Haaland.

Morgan Rogers

Rogers played alongside Palmer and Delap in the 2019/20 FA Youth Cup final but never made a first-team appearance for Manchester City.

He had loan spells at Lincoln City, Bournemouth and Blackpool before joining Middlesbrough on a permanent deal in the summer of 2023.

The 22-year-old midfielder spent just seven months at the Riverside before joining Aston Villa in February 2024, and he has gone from strength to strength at Villa Park.

He has registered nine direct goal contributions in the Premier League this season, including a brilliant goal in Villa’s 2-1 win over City.

“That situation right now, of course these types of players would be with us but it’s always about the right moment,” Guardiola said when asked about the England international.

“I’m happy for him as he’s a lovely guy, he exploded last season and this season. He’s an exceptional player.”

Morgan Rogers makes it 2-0 Aston Villa 🔥 The defensive problems continue for Man City 😳 📺 @tntsports & @discoveryplusUK pic.twitter.com/vuutXbzjas — Football on TNT Sports (@footballontnt) December 21, 2024

Ilkay Gundogan

After captaining City to the Premier League, FA Cup and Champions League titles in 2022/23, Gundogan left on a high and joined Barcelona on a free transfer.

The midfielder spent a year in Spain before returning to City in the summer, but he’s been unable to replicate the form from his first spell at the Etihad.

He looks a shadow of his former self and no longer has the legs needed to compete with some of the game’s more energetic midfielders.

“The game against Newcastle was not really, really good, one of the worst I’ve ever seen from him in the past eight or nine years,” Guardiola said after a 1-1 draw with Eddie Howe’s side.

The decision to re-sign the 34-year-old was seemingly ruled by heart over head and City should’ve targeted a younger midfielder in the summer.

Honourable mentions: Selling Jeremie Frimpong, Pedro Porro, Taylor Harwood-Bellis, Douglas Luiz and Brahim Diaz – all of whom could have become useful assets had they been shown more faith to develop.

READ MORE: Five players Man City must urgently sign replacements for as Guardiola crisis deepens

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