From Drogba to Diomande: Jose Mourinho's 10 most expensive signings

Jose Mourinho has managed some of the biggest clubs in European football - Chelsea, Inter Milan, Manchester United and Real Madrid among them. Naturally, he has also had serious money to spend. Here are the ten most expensive signings of the self-proclaimed Special One's career, counting down to the biggest of them all. 10. Didier Drogba - Chelsea, €38.5m (£33.3m) Mourinho famously moved heaven and earth to convince then-Chelsea owner Roman Abramovich to sign Drogba from Marseille in 2004. It proved to be a defining move. Across Mourinho's two spells at Stamford Bridge, Drogba was central to seven trophies, including three Premier League titles. 9. Tammy Abraham - Roma, €41m (£35.4m) Mourinho took a striker away from Chelsea in 2021, convincing Abraham to leave west London for Rome. The move worked immediately: Abraham scored 27 goals in his debut season and helped Roma lift the UEFA Conference League in 2021-22. 8. Henrikh Mkhitaryan - Man Utd, €42m (£36.3m) Mkhitaryan arrived in the summer of 2016 as part of Mourinho's rebuild at Old Trafford. The Premier League title slipped away in 2016-17, but they ended the season with two trophies, winning the Europa League and the League Cup. 7. Andriy Shevchenko - Chelsea, €43.9m (£37.9m) Unlike the Drogba deal, this one was driven by Abramovich rather than Mourinho. Shevchenko was one of the most feared strikers in the world when he joined in 2006, but he struggled at Chelsea, scoring only four Premier League goals in 2006-07. 6. Nemanja Matic - Man Utd, €44.7m (£38.6m) Mourinho wanted more strength in midfield for 2017-18 and turned to Matic, a player he knew well from Chelsea. United could not collect silverware that season, finishing second in the Premier League and losing in the FA Cup final. 5. Marc Cucurella - Real Madrid, €55m (£47.1m) Mourinho returned to Real Madrid in June 2026, 13 years after his first spell at the club ended, and quickly set about strengthening the defence. Four days after his reappointment, Los Blancos confirmed the signing of Spain defender Cucurella from Chelsea. 4. Fred - Man Utd, €59m (£51m) Fred was linked with Manchester City before choosing United in 2018. He told media he was happy to work with Mourinho and called a match against Tottenham a must-win, but the partnership lasted only six months before Mourinho was sacked in December 2018. 3. Romelu Lukaku - Man Utd, €84.7m (£75m) United signed Lukaku in July 2017, in the same window as Matic. The Belgium striker scored 27 goals in his first season, but United ended 2017-18 without a trophy. 2. Paul Pogba - Man Utd, €105m (£90.8m) Pogba returned to Old Trafford in 2016, four years after leaving United for Juventus, for what was then a world-record fee. Despite winning the Europa League and League Cup, he never consistently matched his form from Italy. 1. Yan Diomande - Real Madrid, €140m (£120m) Diomande had just been named Bundesliga Rookie of the Season for 2025-26 and was wanted by just about every elite club in Europe. The rapid, two-footed winger ended up at Real Madrid, making him Mourinho's most expensive signing.