10 Dramatic Deadline Day Deals That Didn't Materialize

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Adesina David

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May 14, 2023
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There have been some dramatic last-ditch moves across the years on transfer deadline day alongside moves that shockingly failed to materialize.

This transfer has over time been fondly remembered for how they panned out and the nature in which those deals came to fruition or sometimes broke down.

David De Gea, Peter Osaze Odemwingie, Robert Lewandowski, and Mohamed Salah are notable players who were on the brink of moving away from their clubs at the time to other clubs, however, several factors prevented it from seeing the light of day.

Let's take you through some of the most dramatic Deadline Day deals that broke down, with one even as recent as the 2023 summer transfer window.

Mohamed Salah to Al-Ittihad (Saudi Arabia)

The Egyptian was reported to be in for a shocking move to the Saudi Pro League after Al Ittihad tabled a bid of £170 million for his services.

Jurgen Klopp halted the deal from becoming a reality, but it appears it's only a matter of time before Salah might still move to Saudi Arabia.

Peter Odemwingie to Queens Park Rangers (England)

The Nigerian created a memorable deadline day drama when he drove outside Loftus Park in an effort to force a move away from West Bromwich Albion.

However, the deal couldn't see the light of day, which made him gutted, and that also made for an awkward return to training with the Baggies.

Robert Lewandowski to Blackburn Rovers (England)

Blackburn were a side to be reckoned with in English football back in 2010 under the tutelage of Sam Allardyce.

They were keen on signing Lewandowski in that timeframe, but the Barcelona man was prevented from flying to the club because of the eruption of the Icelandic volcano Eyjafjallajokull.

Luckily for Robert Lewandowski, he joined up with Borussia Dortmund subsequently before winning the UEFA Champions League with Bayern Munich years later.

Kaka to Manchester City (England)

The Brazilian had been in talks with Manchester City after the English side declared their interest in his services.

He was set to move for a staggering £100 million on deadline day 2009, but the deal didn't materialize, with Kaka joining Real Madrid 6 months later for a world-record transfer fee.

The 41-year-old later made it known that he rejected City's offer as he was only focused on a move to Real Madrid if he left AC Milan.

Nabir Fekir to Liverpool (England)

Possibly many might still remember this move vividly, with Fekir being linked with a move to the Premier League before he opted to join Spanish La Liga side Real Betis.

The move to Liverpool almost came to pass in 2018, as Nabir Fekir even discussed with Jurgen Klopp and was on the brink of penning a deal with the club before an issue with negotiations hampered the deal from happening.

Joao Moutinho to Tottenham Hotspur (England)

Moutinho was “minutes” away from penning a deal with Spurs in 2012 after the Lillywhites had agreed a £24 million deal with Porto.

However, the paperwork for the deal wasn't submitted to the Premier League in time and Joao Moutinho returned to Portugal before joining AS Monaco 12 months later.

Robinho to Chelsea (England)

Manchester City had just begun moves to flex their muscles in the transfer market and they set their sights on Robinho to begin that quest.

They couldn't land then-Barcelona's Lionel Messi and as such the Cityzens turned their attention to the Brazilian star.

Robinho had been expected to pen a deal with Chelsea, however, Manchester City hijacked the move, with even the footballer stunned that he had joined the Manchester-based club instead of the Blues.

In a presser following the move, Robinho made an error, saying he was happy to be joining “the blues” before he was informed that he had actually joined the Cityzens.

Antonee Robinson to AC Milan (Italy)

This transfer deadline drama is a recent one, in fact, as recent as January 2020, with Robinson closing in on a move to the San Siro before health concerns made the deal not to pull through.

Antonee Robinson, who currently plays for Fulham, was at the time representing Wigan Athletic and he had been dreaming of a move to AC Milan.

However, tests found he had an issue with his heart, and the defender had an insufficient heartbeat, which was due to his intake of caffeine.

After the deal failed to materialize, he joined Fulham and he helped the club secure promotion back to the top-flight.

Ousmane Dembele to Chelsea (England)

The Blues were said to be favorites to land Dembele from Barcelona on deadline day in January 2022, with a certain report claiming the deal was all but sealed.

However, due to time constraints, Chelsea couldn't agree on a deal with the 26-year-old, and as such the transfer couldn't become a reality.

David De Gea to Real Madrid (Spain)

This should arguably be the greatest deadline day drama, with Manchester United having agreed a deal with Real Madrid for the sale of David De Gea.

The Spanish goalie even signed a deal with Los Blancos, but a delay on the path of the Red Devils in returning necessary paperwork alongside the use of a faulty fax machine saw the move go up with the wind.