Liverpool's most memorable transfer collapses including Ronaldo, Remy and Fekir

In football, there's always a chance a move could collapse before the player signs on the dotted line.

Arsenal, for example, almost signed Zlatan Ibrahimovic before his breakthrough at Ajax! Every Premier League club has endured their fair share of near misses in the transfer market... and Liverpool are no different.

The 19-time champions of England have witnessed many players come close to moving to Merseyside in recent years - including a promising Portuguese teenager who's since become a legend in Manchester.

Here, Mirror Football recalls Liverpool's most memorable transfer collapses. It won't be comfortable reading for those who dreamed of a move to Anfield!

Cristiano Ronaldo

What could've been! Liverpool were interested in signing Ronaldo from Sporting Lisbon in the summer of 2003, shortly before his move to Manchester United.

Reds assistant boss Phil Thompson even visited Portugal to watch the teenager in action. He was reportedly keen on a move to Merseyside, yet nothing materialised and he went on to become an icon at Old Trafford instead - winning the Ballon d'Or five times.

"10 days later I was sitting in a lounge at Anfield having some lunch and looking at the big TV screen," recalled Thompson. "Up came the news that Manchester United had signed Ronaldo from Lisbon for £12.2million. Gerard and myself nearly choked on our food!"

Loic Remy

The Frenchman was an immediate hit in the Premier League when he joined QPR from Marseille in January 2013. He scored six goals during the second half of that season and found the back of the net 14 times during a loan spell at Newcastle in 2013-14.

Remy was expected to leave QPR on a permanent deal in the summer of 2014 once his cheap £10.5m release clause was revealed and Liverpool made their move. Yet the deal collapsed when the doctors weren't happy with his routine medical.

"I came for the medical tests and everything was fine and after that they wanted to be sure everything was fine with my heart," said Remy in 2014. "They asked for a specialist for the heart and apparently the guy said they did not 100 per cent agree if I could keep going or had to stop football. I didn't understand because they knew before I came.

"I just told my agent if it is not happening... I was more confused by Liverpool saying that I had medical problem because it is not fair. I have seen the best specialist in London and he has told me I can still play so it was not good from them."

Remy went on to join Chelsea, winning the Premier League and EFL Cup in his first season at Stamford Bridge. The 35-year-old has since played for several clubs - including Crystal Palace - and currently represents Turkish outfit Adana Demirspor.

Teddy Sheringham

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Liverpool manager Roy Evans was keen to bring Sheringham to Anfield in 1995 after he made a prolific start to the Premier League era, scoring 52 goals in the first three seasons of the competition.

Yet the board were unwilling to invest in the England international. He was 29 at the time and they were not interested in signing players over the age of 28. It proved to be a terrible decision as Sheringham continued playing in the Premier League until he was 41!

Sheringham went on to join Man Utd two years later and played a key role in their famous 'Treble' win in 1998-99, scoring the equaliser in the Champions League final victory against Bayern Munich. "He went to play until he was 38, or was it 48?" later joked Evans.

Frank Worthington

The long-haired forward was one of the great mavericks of the 1970s, producing sublime moments of skill on the pitch and enjoying himself off it.

Iconic Liverpool boss Bill Shankly wanted to bring Worthington to Anfield from Halifax in the summer of 1972. After Worthington failed a medical due to high blood pressure, Shankly sent the playboy to Majorca for a week to relax before completing a second medical.

But, according to Yorkshire Live, he also failed that medical after 'encounters' with five women in seven days. Apparently, Worthington's blood pressure was even higher when he returned! Shankly was said to be bemused and cancelled the transfer.

Worthington went on to join Leicester instead. "There was no point in getting upset," he said at the time. "I just told myself it was their loss."

Lee Bowyer

Reds manager Gerard Houllier thought he'd landed a bargain when Leeds midfielder Bowyer became available in the summer of 2002.

The West Yorkshire side were in serious financial trouble and willing to sell Bowyer, their two-time Player of the Year, to Liverpool for £9m. There were concerns about his character following some run-ins with the law, yet Houllier was still keen on a deal.

Once the fee was agreed, fans expected Bowyer to sign a contract. But the transfer dragged on and Houllier pulled the plug for a "variety of reasons" - according to Liverpool's website. "Houllier was not convinced the player had either the hunger or desire to play for the club, qualities which are essential for any Liverpool player," continued the statement.

Bowyer, meanwhile, told BBC Sport: "I never asked to go on the transfer list and made it clear... I had reservations when they accepted Liverpool's bid. So it is probably in the best interest of all parties that the deal did not go through."

Gabriel Heinze

The Argentine defender was a solid performer for Manchester United during his three seasons at Old Trafford, playing 83 games in all competitions to help them win the Premier League in 2006-07. He was even named their Player of the Year in 2004-05.

Yet it was clear Heinze's days were numbered following the arrival of Patrice Evra in January 2006. Liverpool came in for the defender in the summer of 2007 and he was determined to leave, insisting the Reds had met his £6.8m verbal release clause.

Legendary Man Utd boss Sir Alex Ferguson refused to sell Heinze to a rival - a bitter one at that - and the case even went to a tribunal. In the end, Heinze joined Real Madrid that summer and later apologised to Ferguson for his actions.

"I don't have many regrets from my career as a footballer, but that episode with Ferguson [has] to be one of them," said Heinze in 2011. "I'm impulsive and strong-willed and this has got me into trouble at times, which was the case at the time when I left United.

"On reflection, it is easy to see that Ferguson was a major influence on my career, in a positive way... he demands that his players dig as deep for the cause and I'm sorry that we fell out in the final days because I still have so much respect for him."

Nabil Fekir

The France international almost became a Liverpool player in the summer of 2018 when the Reds agreed a transfer fee with Lyon. Fekir, who scored 23 goals in 2017-18, even spoke with Jurgen Klopp about the move before it collapsed in strange circumstances.

"Everything was closed," recalled Fekir in 2021. "I passed all the interviews, I spoke with Jurgen Klopp, he told me that he loved me, we all did it and, when we were about to sign, there were problems with my representative and the negotiation broke down.

"They said it was because I had knee problems, but the truth has been proven over time. My knee is super good."

Fekir went on to join Real Betis 12 months later and has since failed to live up to expectations, scoring just 22 goals in three seasons.