Pep Guardiola, Jose Mourinho and Carlo Ancelotti are among the highest-spending managers in football history, but who has signed the most players?

In today’s game, transfers shape football almost as much as tactics – one successful summer window can completely change a club’s trajectory and transform its fortunes.

With Premier League clubs spending an unprecedented £3.087 billion on new signings in the summer of 2025, the transfer market has never been more influential, especially for managers who regularly overhaul squads rather than work with what they inherit.

As per WinSportsOnline, these are the top 20 football managers with the most signings in history, with Guardiola – the highest-spending manager in football – a notable omission.

20-11. Simeone, Emery and Conte

11-10. Harry Redknapp and Steve Bruce – 117

Sitting joint-10th in this list are two long-serving English managers in Harry Redknapp and Steve Bruce.

Redknapp in particular was famed for his spending whilst in managerial positions, with his most expensive acquisition being Robbie Keane’s arrival at Tottenham Hotspur in February 2009 at around £14million. Managing over a career span of 34 years, Redknapp made 117 purchases, where he enjoyed a strong managerial career in the Premier League.

He is joined by Bruce. The former Manchester United defender made his managerial bow in 1998, and only left his most recent managerial job in October after leaving League One outfit Blackpool.

His most expensive purchase was Joelinton, whilst in charge of Newcastle, coming in at just shy of £40million.

9. Eusebio Di Francesco – 123

Eusebio Di Francesco is still only 56, but that hasn’t stopped him from managing a plethora of clubs from 2008 until now, where he is currently Lecce boss. They face a battle to stay in Serie A, though that isn’t due to a lack of bringing players in, with 13 joining the club over the course of the season.

Di Francesco has signed six more players than the rest, and he made quite a dent in Roma’s budget when he was gaffer at the Stadio Olimpico from 2017 to 2019.

His most expensive purchase was Patrik Schick, who joined for £39million back in July 2018 – only slightly less than Bruce’s major outlay.

8. Rafael Benitez – 124

Back to another boss who used to manage Newcastle United, and Rafael Benitez is seventh on this list with 124 buys, one more than Di Francesco.

Billed as one of the best young managers in the world when he moved from Valencia to Liverpool – and backing that up with a Champions League trophy – he’s since managed an array of clubs such as Inter Milan, Chelsea, Napoli, and Real Madrid.

Although his career is petering out, not least after a poor stint at Everton, he’s still bought well. Fernando Torres, Xabi Alonso and Javier Mascherano joining Liverpool remain two of his better purchases, though his most expensive was the £34.5million move that saw Gonzalo Higuain join Napoli in 2013.

7. Massimiliano Allegri – 127

Sticking to another Serie A managerial icon, and Massimiliano Allegri smashes the record set by any manager in the top ten.

Cristiano Ronaldo’s move from Real Madrid to Juventus came under Allegri’s spell, costing the Turin club £99million.

Elsewhere, he spent £75million taking Higuain to Juventus from Napoli, whilst another seven signings all cost 40 million euros or more. With 127 purchases, his list looks strong.

6. Carlo Ancelotti – 127

Carlo Ancelotti comes in next with 127. That number won’t increase due to his role as Brazilian national team coach, and although he’ll be looking to add a World Cup to his star-studded list of achievements, the Italian has brought in some top players during his managerial career.

Jude Bellingham’s £105million move from Borussia Dortmund to Real Madrid remains his most expensive, but Ancelotti boasts such an impressive CV. Gareth Bale, James Rodriguez and Arda Guler came under his watch at Real, Alessandro Nesta, Kaka and Thiago Silva joined him at AC Milan, whilst Ramires, Daniel Sturridge and David Luiz joined him at Chelsea.

5. Stefano Pioli – 128

Onto another former AC Milan manager, and Stefano Pioli remains a serial spender.

Ousting Ancelotti by just one signing, incredibly his most expensive signing was the £70million to bring Jhon Duran from Aston Villa to Al-Nassr just over a year ago.

However, the majority of his success came at AC Milan. Tijjani Reijnders, Christian Pulisic, Mike Maignan and Sandro Tonali all joined him at the San Siro – which led to Pioli winning the 2021-22 Serie A title.

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4. Jose Mourinho – 136

The self-branded ‘Special One’ was always going to be on this list, and boasting a similar career path to Ancelotti, his move to Chelsea coincided with Roman Abramovich being wiling to get the chequebook out at Stamford Bridge.

Didier Drogba, Michael Essien, Ricardo Carvalho, Paulo Ferreira, Arjen Robben, Petr Cech – the list goes on as Chelsea stormed English football.

But delving deeper into his career, it was in the 2010s that Jose Mourinho properly spent money, especially at Manchester United. Their purchase of Paul Pogba broke the transfer record, whilst Romelu Lukaku and Fred broke the £50m barrier.

Add the signings of Luka Modric, Angel di Maria and Mesut Ozil to his Real Madrid days – and it’s no wonder everyone wanted to play for the Portuguese legend.

3. Claudio Ranieri – 139

Premier League winner with Leicester City, Italian tactician Claudio Ranieri perhaps has the broadest career path on this list, having signed 139 players across 15 different clubs.

Ranieri managed sides in England, Spain, Italy and France during his 39-year coaching career, and most recently was at Roma, where he served as a senior advisor, working alongside manager Gian Piero Gasperini.

Three of Ranieri’s most expensive signings came during his time at Monaco – James Rodriguez, Radamel Falcao and Joao Moutinho – while the remaining two were Hernan Crespo at Chelsea and Islam Slimani at Leicester.

2. Jorge Jesus – 145

Former Benfica and Sporting CP manager Jorge Jesus is now in charge of Saudi Pro League side Al-Nassr, where he coaches the likes of Cristiano Ronaldo, Sadio Mane and Joao Felix.

The 71-year-old spent most of his coaching career in Portugal, where he led Benfica to three Primeira Liga titles and won the League Cup six times – more than any other manager in history.

Unsurprisingly, all six of Jesus’ most expensive signings were made during his time at Al-Hilal, with the top five being Neymar, Malcom, Ruben Neves, Aleksandar Mitrovic and Sergej Milinkovic-Savic.

1. Gian Piero Gasperini – 172

Roma manager Gian Piero Gasperini has made more signings than any other manager – a remarkable 172 – during his three decades on the touchline.

The 68-year-old tactician has spent his entire managerial career in Italy, including nine seasons at Atalanta, where he guided the club to the Europa League title in 2023-24.

Gasperini has also managed Crotone, Genoa, Inter, Palermo and Juventus’ youth side, before being appointed Roma manager in June 2025 on a three-year deal.

His most expensive signing remains El Bilal Toure, who joined Atalanta for €30m in 2023, with Gianluca Scamacca, Mateo Retegui, Raoul Bellanova (all Atalanta) and Wesley (Roma) completing the top five.

Data via WinSportsOnline – correct as of 27/04/26