The 5 players Man Utd tried to sign the last time Cristiano Ronaldo left

Even cave dwellers know that Cristiano Ronaldo left Manchester United for the second time, but the last time he left, leaving for Real Madrid for £80m in the summer of 2009, United suffered a disastrous transfer window.

In what could serve as a warning to Erik ten Hag, United have missed some of the top targets this summer. Ronaldo left, signing Antonio Valencia, Michael Owen and Gabriel Obertan for a total of £20m instead.

We took a look at five attacking players the Red Devils allegedly tried to sign in 2009 to replace Ronaldo and how they have fared since.

Karim Benzema

Benzema first showed United what he was capable of in February 2008, scoring against them for Lyon in a Champions League round of 16 draw.

Sir Alex Ferguson wanted to bring him to Old Trafford 15 months later but faced competition from a greedy Real Madrid side.

As United offered Lyon more money, the striker eventually decided to join Ronaldo and completed a €35m move to Madrid. It was a decision that worked out pretty well to be fair.

The Red Devils then opted for a slightly different option, signing 29-year-old Michael Owen on a free transfer thanks to 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 catch him… [we catch you].'”

Franck Ribery

Regarded as a direct replacement for Ronaldo, Ribéry reportedly wanted to leave Bayern Munich in 2009 after just two years with the Bundesliga side.

According to The Guardian, United have made a £62.5million bid for the winger, who was also linked with Chelsea, Barcelona and – yes, you guessed it – Real Madrid.

"He's fantastic," Ferguson told The Sun in 2009. "Always on the move and with incredible energy. He always goes forward but defends a lot too. He would have no problem playing in England. "

Bayen rejected the offer and convinced Ribéry to stay 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 spell at Bayern in 2019 and only retired in October 2022.

Samuel Eto'o

After scoring Barcelona's first goal against United in the 2009 Champions League final, Eto'o was linked with a move to Old Trafford.

The striker has turned down the chance to join Manchester City and has reportedly hoped to complete an £18m 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 finally arrived in the Premier League with Chelsea in 2013 and scored a hat-trick against David Moyes' United in a 3-1 victory for the Blues.

After spells at Everton, Sampdoria, Antalyaspor, Konyaspor and Qatar SC, he decided to hang up his boots in September 2019.

David Villa

After playing for Spain and Valencia, Villa established himself as one of the most sought-after players in world football in the summer of 2009.

According to AS, United were ready to offer 47 million euros for El Guaje, but he made it clear he didn't want to leave his native Spain.

The striker joined Barcelona in 2010 and scored 48 goals for the club, including a stunning goal against United in the 2011 Champions League final at Wembley.

After battling injuries, Villa left Camp Nou in 2013 and spent a season at Atletico Madrid, where they won a third La Liga title.

The 39-year-old saw his playing career in America, Australia and Japan before announcing his retirement in November 2019.