Football history is full of “what if” moments, and transfer windows produce some of the best ones. For every deal that gets done, there’s another that collapses at the last minute, gets vetoed by an owner, or simply falls apart over a plane that never took off. Here are some of the biggest Premier League transfers that came agonizingly close to happening but never did.

Roy Keane Very Nearly Became a Blackburn Player

Before he became a Manchester United icon and lifted seven Premier League titles, Roy Keane had effectively agreed to join Blackburn Rovers from Nottingham Forest in 1993. A handshake deal with manager Kenny Dalglish was in place and the contract was close to finalized. A call from Manchester United changed everything, and Keane switched his signature to Old Trafford instead, going on to captain the club through its most dominant era.

Zinedine Zidane Nearly Landed at Blackburn Too

Blackburn came agonizingly close to landing a genuine legend just a year later. Fresh off winning the 1994-95 title, the club identified a young French midfielder as the perfect signing to help defend their crown: Zinedine Zidane. He and Bordeaux teammate Christophe Dugarry actually visited Blackburn’s training ground for talks, only for the move to be vetoed by the club’s ownership. Three years later, Zidane won the World Cup with France, and he added the Ballon d’Or the same year.

Alan Shearer’s Manchester United Flirtation

The Premier League’s all-time top scorer very nearly wore red instead of black and white stripes. Alan Shearer held serious talks with Manchester United about a move before ultimately deciding to join Newcastle United instead, in what was a world-record transfer at the time. Shearer went on to score 148 of his 260 Premier League goals for his boyhood club.

A Young Zlatan Snubbed by Arsenal

Long before he became one of football’s most recognizable personalities, a 17-year-old Zlatan Ibrahimovic travelled to London for talks with Arsenal and even posed for photos in the club’s shirt. The move fell apart when Arsene Wenger insisted on giving him a trial first, an approach the young Swede reportedly found insulting. Ibrahimovic eventually did arrive in the Premier League, but not until 16 years later, when he signed for Manchester United instead.

Cristiano Ronaldo’s First Brush with Arsenal

Wenger has since called this one of his biggest regrets. In 2003, he hosted a 17-year-old Cristiano Ronaldo and his mother for lunch at Arsenal’s training ground, hoping to sign him from Sporting Lisbon. The deal ultimately came down to fee negotiations, and Ronaldo signed for Manchester United instead, where he’d go on to win three Premier League titles before later claiming multiple Ballon d’Ors elsewhere in his career.

Robert Lewandowski and the Volcano That Changed Everything

One of football’s stranger near-misses involves a natural disaster. Blackburn Rovers had a deal in place to sign a young Robert Lewandowski from Lech Poznan, but his flight to England was cancelled after a volcanic ash cloud grounded flights across Europe in 2010. The deal never got back on track, and Lewandowski instead built his career at Borussia Dortmund, Bayern Munich, and Barcelona.

Kylian Mbappe Twice Turned Down Premier League Giants

Two of the Premier League’s most iconic managers both tried and failed to land Kylian Mbappe before he became a global superstar. Arsene Wenger personally flew to meet a 17-year-old Mbappe and his family in an attempt to bring him to Arsenal, and a year later Jurgen Klopp made a similar push for Liverpool. Mbappe chose Paris Saint-Germain instead, where he spent six years and won a World Cup before eventually moving to Real Madrid.

Erling Haaland Almost Joined Manchester United First

City fans might be uneasy reading this one. In 2019, then-Manchester United manager Ole Gunnar Solskjaer flew to Austria to try to convince fellow Norwegian Erling Haaland to join United from Red Bull Salzburg. The move fell through, and Haaland instead signed for Borussia Dortmund before eventually joining Manchester City, where he’s since won multiple Premier League titles and Golden Boots.

Jude Bellingham’s Old Trafford Meeting

Manchester United rolled out serious star power in an attempt to sign a teenage Jude Bellingham, with club legends joining talks at the training ground to help make the case. Despite what was reportedly a positive meeting, Bellingham chose Borussia Dortmund instead, before making his high-profile move to Real Madrid a few years later.

Why These Moments Matter

What makes these near-misses so fascinating isn’t just the size of the names involved; it’s how differently football history could have looked with a single decision going the other way. A volcano, a veto, a missed phone call, or a demanded trial were each enough to send a future superstar down a completely different path, and Premier League fans have been left wondering “what if” ever since.