Given Spain’s rather lacklustre performance in their 0-0 draw against tiny Cape Verde, La Roja fans may be wondering if their players would be better concentrating on getting results for the national side in the World Cup rather than getting distracted with dream transfers.
Spain, one of the pre-tournament favourites, were frustrated in their 2026 World Cup opener on the 15th of June. However, at almost exactly the same time, their left-back, Chelsea player Marc Cucurella, saw his move to Real Madrid officially completed. It was strange timing and an odd move in general, with the player seemingly a very good fit for the new Blues boss, Xabi Alonso. One thing that was not unusual, however, was a player moving from Stamford Bridge to the Bernabeu.
In recent years, we have seen lots of links between these two teams. And of course, they have not been limited only to players.
Can Alonso Thrive at Chelsea?
The obvious place to start is the man who sold Cucurella to Real, the coach who will have managed both teams during 2026. Alonso is yet to take charge of a Chelsea game, but Blues fans will be excited about his appointment, announced in May 2026 and set to start on the 1st of July.
Alonso was hugely successful with Bayer Leverkusen but despite winning over 70% of his games as Real Boss, the Spaniard left the club by “mutual consent” in January 2026. It will be very interesting indeed to see how the former Liverpool star gets on in west London.
Jose Mourinho, a Man Who Loves Returns
In life and football, it is often said that you should never go back. Players and managers who return to a club where they previously enjoyed success rarely do as well the second time around. That adage, however, has not deterred Real Madrid from reappointing Jose Mourinho.
The Special One was in his second stint as Benfica boss when Real Madrid came calling. The Portuguese managerial megastar also had two separate spells at Chelsea. Second time round, he managed to win the Premier League and the League Cup, but his return was still nowhere near as successful as his first stint in west London.
Madrid, who announced they had made Mourinho their manager once again on the 11th of June 2026, will be hoping that pattern will not repeat in Spain. That said, after a trophyless 2025/26, they would certainly take another La Liga title and a cup in Mourinho’s first season back in the Spanish capital.
He first took charge of Los Blancos in 2010 and stayed for three years. He won almost 72% of the 178 games he was in the dugout for and led them to La Liga glory in 2011/12. It was a record-breaking campaign too, with Mourinho showing his ability to adapt and playing exciting football, his free-scoring side dominating domestically. They won the title by nine points and scored a frankly insane total of 121 goals in 38 matches. Those are stats the Real fans and the club’s hierarchy will be desperate to see return. Sadly, they won’t have a peak-era Cristiano Ronaldo at their disposal this time.
Eden Hazard
Eden Hazard said in May 2026 that he never felt he had moved to Madrid to replace Ronaldo. CR7 moved from Real to Juventus in the summer of 2018, with Hazard leaving the Bridge around a year later. Much as he might claim he was not there to take over from the Portuguese icon… he was.
Hazard had been brilliant for Chelsea, netting 44 PL goals in 107 games in his final three seasons in English football. In total, he scored 55 times across those campaigns, but he also assisted many more. His balance and mesmeric dribbling created time and space for others as well and he was named Premier League Player of the Season in 2014/15. That season he won the awards treble, being crowned PFA Players’ Player of the Year and winning the Football Writers’ honour too.
Chelsea’s Player of the Year for four seasons was the leading assist maker at Euro 2016 and won the Silver Ball at the 2018 World Cup. However, his time at Real was simply a disaster. Hindered by injuries more than anything else, the Belgian played just 76 times for Madrid, scoring seven goals. That was scant return for the £90m plus add-ons Real paid the Blues and they will certainly be hoping the £52m they have paid for Cucurella will prove better value.
Another Brilliant Belgian
Thibaut Courtois was another brilliant Belgian who has played for both clubs, but he managed to be successful with both. The giant stopper signed for Chelsea from Genk in 2011 for around €9m but was sent to Atletico Madrid on loan. His loan was extended twice, meaning in all he played three seasons with Atleti, establishing himself as a world-class goalie over 154 games in the Spanish capital.
He returned to the Blues for the 2014/15 season and was a regular fixture over the next four campaigns. He won two league titles and a League Cup with Chelsea, as well as the PL Golden Glove award in 2016/17. After excelling at the 2018 World Cup for Belgium, for whom he has won over 100 caps, he moved back to Madrid, but this time to Real. Chelsea made a nice profit, selling him for £35m.
He took a little while to settle but then established himself as one of the greats by keeping 17 clean sheets in the 2019/20 campaign, helping Madrid to the title. Perhaps his best moment in the white of his current club came in the 2021/22 Champions League final. He made nine saves, some of them real worldies, as his side beat Liverpool 1-0 and he was named Man of the Match.
Rugged Rudiger a Steal
In recent years, Madrid have moved away from the Galactico transfer policy of the past and have preferred to pick up high-class players who are out of contract. They got Rudiger on a free after his Chelsea contract expired and the rugged German international has been a key part of their team.
Chelsea bought him from Roma for around £29m in 2017. During his five seasons at the club he played over 200 games. He won the FA Cup, the Champions League, the Europa League and the Club World Cup with the Blues. More silverware has followed with Real, including a 2023/24 Liga/Champions League double, the Spanish Cup and another Club World Cup.
Other Chelsea and Real Connections
There are various other players and managers who have been at both of these great clubs. These include:
- Claude Makelele – a brilliant defensive midfielder, played 217 times for Chelsea after 145 appearances for Real
- Mateo Kovacic – another defensive midfielder Chelsea signed from Real, the Austrian-born Croatian has also played for Inter Milan and left Chelsea for Man City
- Guus Hiddink – brilliant Dutch boss Hiddink was only in charge of Real for 34 games, during the first part of the 1998/99 campaign. He had two stints at Stamford Bridge, both as caretaker boss
- Rafa Benitez – Benitez perhaps enjoyed most success with Valencia and Liverpool, although he did guide Chelsea to the Europa League in 2012/13. He was in charge for just 25 games at the Bernabeu and 48 at the Bridge, despite being a caretaker only for the Blues