15 Premier League Transfers That Almost Happened
There is a parallel history of the Premier League that never quite happened. A league where Roy Keane never snarled in a Manchester United shirt, where Cristiano Ronaldo twisted full-backs at Highbury, where Blackburn Rovers lined up with Zinedine Zidane and Robert Lewandowski, and where Erling Haaland bullied defences in red, not sky blue.
Football never stands still, but some sliding doors never stop rattling. Here are 15 of the biggest Premier League transfers that came close, then vanished.
Keane and Zidane: Blackburn’s lost empire
Before he became the snarling heartbeat of Manchester United’s dominance, Roy Keane had already given his word elsewhere.
In 1993, the Irish midfielder shook hands with Kenny Dalglish and agreed to join Blackburn Rovers from Nottingham Forest. The deal was there. The contract was “basically agreed”. Keane went home to Ireland, only for Manchester United to call. One phone call, one change of mind, and the course of English football changed. Seven Premier League titles later, four as captain, Old Trafford had its icon – and Blackburn had a what-if that still stings.
Two years on, Blackburn flirted with another era-defining midfielder. Fresh from winning the 1994/95 Premier League title, Dalglish targeted a young Zinedine Zidane at Bordeaux, along with Christophe Dugarry. They came to the training ground. They spoke to owner Jack Walker. Then came the veto and the infamous line that still echoes around Ewood Park: “Why do you want to sign Zidane when we have Tim Sherwood?”
Within three years, Zidane was a World Cup winner and Ballon d’Or holder. Blackburn, meanwhile, were drifting away from the summit they had briefly scaled.
Shearer’s fork in the road
In the summer of 1996, Alan Shearer stood at a crossroads that would define his legacy.
Manchester United wanted him. Newcastle United wanted him. He sat down with Sir Alex Ferguson and Kevin Keegan on the same day. By his own admission, he was “90 per cent” sure he would join United. The goals, the trophies, the medals – all seemed set to flow at Old Trafford.
Then Keegan called again. The pull of his boyhood club proved stronger than Ferguson’s empire. Shearer chose Newcastle for a world record £15 million fee. He became the Premier League’s all-time leading scorer with 260 goals, 148 of them in black and white. He never lifted the league title. But he became a monument on Tyneside.
West Ham’s £1m gamble they didn’t take
In 1999, West Ham United had a teenage Andriy Shevchenko on trial.
Harry Redknapp watched the 17-year-old Ukrainian score twice in a game against Barnet reserves. The staff liked him. The fee? Around £1 million. Too steep, they decided, for a kid from Dynamo Kyiv’s system.
West Ham walked away. Shevchenko went on to win the Ballon d’Or in 2004 and terrorised Europe with Dynamo and AC Milan before finally arriving in the Premier League with Chelsea in 2006. By then, the bargain had long gone.
Wenger’s nearly men: Zlatan, Yaya and Ronaldo
Few managers sit on a bigger pile of transfer near-misses than Arsene Wenger.
At the turn of the millennium, a 17-year-old Zlatan Ibrahimovic flew in from Malmo. Arsenal printed a No 9 shirt with “Ibrahimovic” on the back and he posed for photos. The club wanted a trial first. Zlatan refused to “do auditions” and walked away. Sixteen years later, he finally came to England – for Manchester United, not Arsenal.
In 2003, another future Premier League great briefly wore Arsenal colours. Yaya Toure, then at Beveren, played a pre-season friendly against Barnet while on trial. Wenger wanted to sign him, but the work permit dragged on. Toure grew impatient and joined Metalurh Donetsk, a move that required no passport complications. Years later, he returned to England as the driving force of Manchester City’s midfield, winning three Premier League titles between 2010 and 2018.
That same year, 2003, Wenger came agonisingly close to the one that still haunts him: Cristiano Ronaldo. Arsenal hosted the 17-year-old Sporting Lisbon winger and his mother at their training ground. He was given a shirt with his name on the back. The club tried to close the deal, but the transfer fee became the sticking point. Manchester United stepped in, paid the price, and watched Ronaldo win three Premier League titles and five Ballons d’Or across a glittering career.
Ronaldinho, Rivaldo and the Premier League that never was
For a brief window in 2003, it looked as though Ronaldinho would dazzle Old Trafford.
He had decided to leave Paris Saint-Germain, and Manchester United believed they were “very close” to sealing a deal. The Brazilian playmaker was on the brink of becoming the new star of Ferguson’s side. Then Barcelona moved. Sandro Rosell promised him Camp Nou if he became president, and Ronaldinho said yes. He went on to win the Ballon d’Or in 2005 and the Champions League in 2006, his genius lighting up La Liga instead of the Premier League.
A year later, another Brazilian great almost chose one of English football’s unlikeliest stages. In 2004, World Cup winner and Ballon d’Or recipient Rivaldo was a free agent and on the verge of joining Sam Allardyce’s Bolton Wanderers. The club had a fax confirming he wanted to come. The financial terms were agreed. Rivaldo even spoke of the “challenge” of taking Bolton into Europe for the first time in their history.
The ink never hit the paper. The deal collapsed, and Rivaldo signed for Olympiacos. Bolton’s dream of a global superstar in white disappeared as quickly as it had appeared.
Gerrard’s Chelsea temptation
Few transfer sagas have cut as deeply as Steven Gerrard’s flirtation with Chelsea in 2005.
Fresh from leading Liverpool to that miraculous Champions League triumph in Istanbul, Gerrard was the player Jose Mourinho wanted above almost all others. Mourinho imagined a midfield of Claude Makelele, Gerrard and Frank Lampard – a terrifying blend of power, control and goals.
The pursuit worked. Gerrard submitted a transfer request. He admitted later that Mourinho had “turned my head” and that he was tempted by the idea of playing under the Portuguese coach. Chelsea stood ready to pounce. Then came the late twist. After talks with his family, Gerrard stayed. He signed a new four-year contract and remained at Anfield for another decade, becoming the symbol of Liverpool’s modern era.
Ramsey’s detour to Arsenal
In 2008, Manchester United believed they had stolen a march on their rivals.
The club announced they had agreed a fee with Cardiff City for Aaron Ramsey, describing the 17-year-old as one of Wales’ brightest prospects. The deal looked done. Ten days later, Ramsey signed for Arsenal instead.
Wenger flew him out during Euro 2008, grabbed a few hours away from punditry duties and sold him the club’s vision over lunch. Ramsey felt wanted. Over the next 11 years, he repaid that faith with three FA Cup wins and a catalogue of big-game goals.
Lewandowski and the volcano that saved Europe
Blackburn Rovers were back at the brink of something big in 2010.
They had agreed a proposal with Lech Poznan and Robert Lewandowski. The striker was due to fly to England, see the club, the stadium, the facilities, and likely sign. Then nature intervened. The Eyjafjallajokull volcano in Iceland erupted, grounding flights across Europe. Lewandowski never made it to Blackburn.
He joined Borussia Dortmund instead, then Bayern Munich, then Barcelona. He became the third-highest scorer in Champions League history and one of the most prolific forwards of his generation. Blackburn, once again, were left to imagine what might have been.
Mbappé: Wenger and Klopp’s shared frustration
Before Kylian Mbappé became a World Cup winner and global superstar, two Premier League giants tried to lure him away from Monaco.
In 2016, Wenger flew to the south of France to sit in the Mbappé family home, trying to convince the 17-year-old to join Arsenal before he signed his first professional contract. A year later, Jürgen Klopp launched Liverpool’s charm offensive. The club took Mbappé and his family on a private jet, circled in the sky, talked, dined, and laid out their vision.
Liverpool “pulled out all the stops”. Arsenal had made their pitch. Mbappé chose Paris Saint-Germain. He dominated Ligue 1, won the World Cup with France in 2018, and eventually joined Real Madrid. English football watched from afar.
Haaland and Bellingham: United’s modern regrets
Manchester United’s recent history is littered with near-misses of its own.
In December 2019, Ole Gunnar Solskjaer pushed hard to sign Erling Haaland from Red Bull Salzburg. Solskjaer knew him well from their time together at Molde and even flew to Austria for talks. He had already phoned United 18 months earlier, urging them to sign the young striker, insisting he would be “absolutely top class”. The club hesitated then, and when they finally moved, they were no longer alone. Haaland chose Borussia Dortmund.
He eventually arrived in Manchester in 2022 – but at City. Two Premier League titles, three Golden Boots and a torrent of goals have underlined exactly what United passed up.
The story with Jude Bellingham is no less painful. In 2020, the 17-year-old Birmingham City midfielder visited United’s Carrington training ground with his family. Solskjaer, Sir Alex Ferguson, Bryan Robson and Eric Cantona were all there, selling the club, the history, the future. Those in the room left convinced he would sign.
He didn’t. Bellingham joined Borussia Dortmund, then Real Madrid in 2023, emerging as one of the defining midfielders of his generation. United were left with another near-miss on an already crowded list.
Football’s history books are written by the players who signed. But the stories fans tell, late at night and over pints, often belong to those who didn’t. Keane in blue and white. Zidane at Ewood. Ronaldo at Highbury. Haaland in red.
How different would the Premier League look if even a handful of these deals had gone through?
