Six former players Jose Mourinho could sign at Benfica, including ex Man Utd stars

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David de Gea, Jose Mourinho and Karim Benzema

Mourinho has worked with some great players in his career

Jose Mourinho has been appointed as the new Benfica manager and will already start to look at how he can improve their squad in the transfer market.

Mourinho began his managerial career with Benfica back in 2000 but took charge of only 11 games and left following a dispute with the club president.

He’s since worked at Porto, Chelsea, Inter Milan, Manchester United, Tottenham, Roma and most recently, Fenerbahce, establishing himself as one of the greatest managers of all time over one of the most colourful managerial careers of the modern generation.

We’ve taken a look at six players Mourinho has previously worked with and could now try to bring to Benfica.

David de Gea

Mourinho spent two and a half seasons in the Manchester United dugout and De Gea was widely regarded as the best goalkeeper in the world during that period.

The Spain international was named in the Premier League Team of the Season in 2017/18 and won the Golden Glove after keeping 18 clean sheets. He also won both the Sir Matt Busby Player of the Year award and the Players’ Player of the Year award at United.

“We’ve got a great manager,” De Gea said in 2018. “He’s very experienced, he’s won everything there is to win in the game. What he is really good at is transmitting his winning mentality to the group.”

His form dipped following Mourinho’s departure and Erik ten Hag allowed the goalkeeper to leave Old Trafford on a free transfer at the end of the 2022/23 season.

He spent the entire 2023/24 campaign without a club before joining Fiorentina in August 2024 and has since been one of the standout performers for the Serie A side.

The 34-year-old recently signed a contract extension until 2028 but the deal reportedly includes a release clause that will let him leave for a ‘relatively small sum’.

Nacho Fernandez

A Real Madrid academy graduate, Nacho made his senior debut under Mourinho in a 6-3 win away at Valencia in April 2011.

The defender went on to make another 363 appearances for Madrid, winning four La Liga titles, six Champions Leagues, two Spanish Cups, five Club World Cups, four European Super Cups and five Spanish Super Cups.

“I am proud of him,” Mourinho said. “He was a kid but with the mentality of a man. It was easy to see his potential at every level. From that Valencia match until the Champions League final, I can only say that I am so proud of him.”

The 35-year-old is now playing for Saudi Pro League club Al-Qadsiah but has entered the final year of his contract and would add more leadership and experience to the Benfica squad.

Sergio Reguilon

Reguilon joined Tottenham from Real Madrid in a £32million deal in the summer of 2020 and loved working under Mourinho in north London.

“Mourinho impressed me a lot,” he said in 2020. “Since I was kid I really liked him, I like his intensity in training. I would like if people saw him as I see him now. He is the first to be serious and ask more from us but when it’s time to fool around, he is also the first.”

But Spurs sacked Mourinho in April 2021 and the left-back subsequently fell out of favour, spending time on loan at Atletico Madrid, Manchester United and Brentford.

The manager reportedly tried to sign him at Fenerbahce, and he is now available on a free transfer after his Tottenham contract expired at the end of last season.

While Samuel Dahl is currently the first-choice left-back at Benfica, Reguilon would still be a shrewd addition to the squad.

Nemanja Matic

Matic first played under Mourinho following his return to Chelsea in January 2014 and was a mainstay in the side that secured a League Cup and Premier League double in 2014/15.

The manager brought the midfielder to Manchester United in a £40million deal in the summer of 2017 and they linked up for a third time at Roma five years later.

Across those three clubs, he has made 209 appearances under Mourinho and is his fifth most-used player after Ricardo Carvalho, John Terry, Frank Lampard and Paulo Ferreira.

“With Jose Mourinho, my connection is obviously football, through three clubs: Chelsea, Manchester United, and Roma,” he said. “So I have a special relationship with him. I appreciate him both as a coach and as a person.

“He was a very important coach in my career; there’s nothing to hide. For me, he’s one of the best coaches in the history of football. He’s special because after him, many wanted to be like him.

“He transformed football, especially in the Premier League. He’s special for everyone, and especially for me, because I spent a lot of time with him.”

While Matic recently joined Sassuolo on a free transfer, he only signed a one-year contract with the Serie A side and previously spent three years at Benfica between 2011 and 2014.

Jesse Lingard

Lingard netted the first goal of the Mourinho era at Manchester United with a brilliant solo strike in the 2-1 win over Leicester City in the 2016 Community Shield.

He also scored the opener in the 2016/17 EFL Cup final win over Southampton and then registered 13 goals and seven assists in all competitions in 2017/18.

“Me and Jose had a good relationship generally, though, I have to say,” he wrote for The Players Tribune. “He was good to me. Before all the injury stuff, he trusted me, put me in for important games. We won trophies and he made me a winner. He could just bring out that side in you.

“He also liked to have a personal connection with his players. Sometimes I’d look at my phone and I’d be getting a random FaceTime from him. Just out of nowhere — just to check in.”

The attacking midfielder was linked with a reunion with Mourinho at Roma following the expiration of his United contract in 2022 but that move failed to materialise.

He is now playing in South Korea for FC Seoul and his contract expires at the end of December, although the K-League side do have an option to extend his deal by a further 12 months.

The 32-year-old may still be looking for a return to European football and could be about to receive another FaceTime from Mourinho.

Karim Benzema

After a difficult debut season at Real Madrid in 2009/10, Benzema improved following Manuel Pellegrini’s departure and Mourinho’s arrival.

The striker scored 78 goals and provided 43 assists in 150 games under the Portuguese tactician, and the duo won one La Liga title and one Copa Del Rey trophy together.

“Mourinho helped me a lot,” he admitted. “It’s his character. It stings you every time [he criticises you] and you surpass yourself on the field. He is a good coach.”

While Mourinho was sacked by Madrid in 2013, Benzema remained at the Bernabeu until 2023 and is the second-highest goal scorer in the club’s history after Cristiano Ronaldo.

“I love him and he knows that and I hope I could give him something in that time we spent together,” Mourinho said. “Three years. I’m pretty sure I gave him something.”

The 37-year-old has now entered the final year of his contract with Saudi Pro League club Al-Ittihad and Mourinho might try to bring him to Benfica, although he would need to take a huge pay cut.

READ MORE: Ranking Mourinho’s first signing at each club from best to worst: Real Madrid superstar to Tottenham stinker

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