After selling Cristiano Ronaldo to Real Madrid for £80million, Manchester United endured a disastrous transfer window in the summer of 2009.
United missed out on some top targets, signing Antonio Valencia, Michael Owen and Gabriel Obertan for a combined £20million instead.
We’ve taken a look at five players they reportedly tried to sign in 2009 to see how they’ve fared since.
Benzema first showed United what he was capable of in February 2008, scoring against them for Lyon in a Champions League last-16 tie.
Sir Alex Ferguson wanted to bring him to Old Trafford 15 months later but faced competition from a very greedy Real Madrid side.
While United offered more money to Lyon, the striker ultimately decided to join Ronaldo and completed a €35million move to Madrid.
The Red Devils then went for a slightly different option, signing a 29-year-old Michael Owen on a free transfer courtesy of a brochure.
“I only came to United because he [Benzema] chose Real Madrid instead of United,” Owen told BT Sport in 2021. “The first time I got a call from Sir Alex Ferguson, he said, ‘We want to sign Benzema, if we don’t get him… (we’re getting you).’”
The France international remains at Madrid to this day, having netted 279 goals in 559 appearances for the club, making him their fifth-highest goalscorer of all time.
Regarded as a direct replacement for Ronaldo, Ribery reportedly wanted to leave Bayern Munich in 2009 after just two years with the Bundesliga side.
According to The Guardian, United made a £62.5million bid for the winger, who was also linked with Chelsea, Barcelona and – yes, you guessed it – Real Madrid.
“He is fantastic,” Ferguson told The Sun in 2009. “Always moving and incredible energy. He is always going forward but defends a lot too. He would have no problem playing in England.”
Bayen rejected the bid and convinced Ribery to remain at the Allianz Arena, where he developed a brilliant partnership with Arjen Robben and became one of the best players in the world.
The 38-year-old ended his 12-year stay at Bayern in 2019 and is now rolling back the years at Serie A side Fiorentina.
After scoring Barcelona’s first goal against United in the 2009 Champions League final, Eto’o was then linked with a move to Old Trafford.
The striker turned down the chance to join Manchester City and was reportedly hopeful of completing an £18million move to United.
But he became a pawn in a swap move for Zlatan Ibrahimovic, joining Inter Milan before winning his second consecutive treble in 2009-10.
Eto’o eventually arrived in the Premier League with Chelsea in 2013 and famously scored a hat-trick against David Moyes’ United in a 3-1 win for the Blues.
After spells at Everton, Sampdoria, Antalyaspor, Konyaspor and Qatar SC, he decided to hang up his boots in September 2019.
When Samuel Eto’o destroyed Manchester United 🔥pic.twitter.com/56dOOiILLl
— Goal (@goal) August 29, 2020
Having starred for Spain and Valencia, Villa established himself as one of the most highly sought-after players in world football in the summer of 2009.
According to AS, United were ready to offer €47million for El Guaje, but he made it clear that he didn’t want to leave his native Spain.
The forward joined Barcelona in 2010 and went on to score 48 goals for the club, including a stunning strike against United in the 2011 Champions League final at Wembley.
After struggling with injuries, Villa left Camp Nou in 2013 and spent a season at Atletico Madrid, where he claimed a third La Liga title.
The 39-year-old saw out his playing career in America, Australia and Japan before announcing his retirement in November 2019.
The second former Valencia player to feature on this list, Silva was heavily linked with United, but a move to Old Trafford failed to materialise.
“It is true that there was a bid from a big English club,” Silva said in September 2009. “If it was only a question of money then I would have accepted the move.”
The midfielder spent another year at the Mestalla before landing in the blue half of Manchester, completing a £25million move to City.
He then became a thorn in United’s side, helping City win four Premier League titles, two FA Cups and five League Cups during his 10 years at the Etihad.
The 35-year-old returned to Spain with Real Sociedad in 2020 and lifted the Copa del Rey in his debut season.